O-benzyloxime ethers and crop protection agents containing these compounds

ABSTRACT

O-Benzyloxime ethers of the formula Iwherein5 x is substituted or unsubstituted CH2, NOalkylY is O, S, NR5R1, R2, R5 are H, alkylZ1, Z2 are H, halogen, methyl, methoxy, cyanoR3, R4 are hydrogen, cyano, substituted or unsubstituted alkyl, alkenyl, cycloalkyl, cycloalkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, benzylthio, alkylcarbonyl, substituted or unsubstituted benzylcarbonyl, alkoxycarbonyl, substituted or unsubstituted phenoxycarbonyl substituted or unsubstituted benzyloxycarbonyl,N(R6)2, where R6 is H, alkyl, substituted or unsubstituted phenyl,-CO-N(R7)2, where R7 is H, substituted or unsubstituted alkyl,substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted hetaryl, substituted or unsubstituted hetaryloxy, substituted or unsubstituted hetarylthio, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclyloxy,R3 and R4 together may form a carbocyclic or heterocyclic ring which is substituted or unsubstituted, andR3 or R4 may be halogen, ormay bewheren is an integer from 1 to 4, andR8 is, or, when n&gt;1, the R8&#39;s are identical or different and are each, H, halogen, cyano, nitro or substituted or unsubstituted C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, aryl, aryloxy, benzyloxy, hetaryl or hetaryloxy,and crop protection agents containing these compounds.

The present invention relates to novel O-benzyloxime ethers and a method for controlling pests, in particular fungi, insects, nematodes and spider mites with these compounds.

It is known that substituted phenylacetic acid oxime derivatives can be used as fungicides (European Patent 253,213). However, their action is unsatisfactory.

We have found, surprisingly, that O-benzyloxime ethers of the general formula I

where

X is CH₂, CH—C₁-C₄-alkyl, CH—C₁-C₄-alkoxy, CH—C₁-C₄-alkylthio or N—C₁-C₄-alkoxy,

Y is O, S or NR⁵,

R¹, R² and R⁵ are each H or C₁-C₄-alkyl,

Z¹ and Z² are identical or different and are each H, halogen, methyl, methoxy or cyano,

R³ and R⁴ are identical or different and are each hydrogen, cyano, straight-chain or branched C₁-C₁₀-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄alkylthio-C₁-C₄-alkyl, arylthio-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₅-haloalkenyl, C₃-C₆-cycloalkenyl, C₃-C₆-halocycloalkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, benzylthio, C₁-C₄-alkylcarbonyl, unsubstituted or substituted phenylcarbonyl, unsubstituted or substituted benzylcarbonyl, C₁-C₄-alkoxycarbonyl, unsubstituted or substituted phenoxycarbonyl, unsubstituted or substituted benzyloxycarbonyl, unsubstituted or substituted aryl, unsubstituted or substituted aryloxy, unsubstituted or substituted arylthio, unsubstituted or substituted aryl-C₁-C₄-alkyl, unsubstituted or substituted aryl-C₁-C₄-alkenyl, unsubstituted or substituted aryloxy-C₁-C₆-alkyl, unsubstituted or substituted arylthio-C₁-C₄-alkyl, unsubstituted or substituted hetaryl, unsubstituted or substituted hetaryloxy, unsubstituted or substituted betarylthio, unsubstituted or substituted hetaryl-C₁-C₄-alkyl, unsubstituted or substituted hetaryl-C₂-C₄-alkenyl, unsubstituted or substituted heteryloxy-C₁-C₄-alkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted heterocyclyloxy, N(R⁶)₂, where the radicals R⁶ are identical or different and are each H, C₁-C₄-alkyl or unsubstituted or substituted phenyl, or

—CO—N(R⁷)₂, where the radicals R⁷ are identical or different and are each H or C₁-C₄-alkyl, substitutents, in addition to hydrogen, being halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, C₁-C₁₀-alkoximino-C₁- or C₂-alkyl, aryl, aryloxy, benzyloxy, hetaryl, hetaryloxy, C₃-C₆-cycloalkyl, heterocyclyl or heterocyclyloxy, or

R³ and R⁴ together may form a carbocyclic or heterocyclic ring which may be substituted by the above-mentioned substituents, and

R³ or R⁴ may be halogen, or

may be

where

n is an integer from 1 to 4, and

R⁸ is, or, when n>1, the R⁸'s are identical or different and are each, H, halogen, cyano, nitro or substituted or unsubstituted C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄haloalkyl, C₁-C₄-haloalkoxy, aryl, aryloxy, benzyloxy, hetaryl or hetaryloxy,

have excellent fungicidal, insecticidal, nematicidal and scaricidal activity which is better than that of the known phenylacetic acid derivatives.

The fungicidal action is preferred.

The radicals stated for the general formula I may, for example, have the following meanings:

X may be C₁-C₄-alkylidene (eg. methylidene, ethylidene, nor isopropylidene, n-, iso-, sec- or tert-butylidene),

C₁-C₄-alkoxymethylidene (eg. methoxy-ethoxy-, n-propoxy, isopropoxy-, n-butoxy-, isobutoxy-, sec-butoxy- or tertbutoxymethylidene), C₁-C₄-alkylthiomethylidene (eg. methyl-, ethyl-, n-propyl-, isopropyl-, n-butylthio-, isobutylthio-, sec-butylthio- or tert-butylthiomethylidene) or C₁-C₄-alkoximino (eg. methoximino, ethoximino, n-propoximino, isopropoximino, n-butoximino, isobutoximino, sec-butoximino or tert-butoximino),

Y may be O, S or NR⁵,

R¹, R² and R⁵ may each be H or C₁-C₄-alkyl (eg. methyl, ethyl, n- or isopropyl, n- or iso-, sec- or tert-butyl),

Z¹ and Z² may be H, halogen (eg. fluorine, chlorine, bromine or iodine), methyl, methoxy or cyano, and

R³ and R⁴ may be identical or different and are each hydrogen, cyano, straight-chain or branched C₁-C₁₀-alkyl (eg. methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, n-, iso-, sec-, tert- or neopentyl, n-hexyl or n-decyl), C₁-C₄-haloalkyl (eg. trifluoromethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, fluorodichloromethyl, difluorochloromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2-chloroethyl, 2,2,2-trichloroethyl or pentachloroethyl), C₃-C₆-cycloalkyl (eg. cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl), C₃-C₆-halocycloalkyl (eg. 2,2-difluorocyclopropyl, 2,2-dichlorocyclopropyl, 2,2-dibromocyclopropyl, 2,2-dichloro-3-methylcyclopropyl or tetrafluorocyclobutyl), C₃-C₈-cycloalkyl-C₁-C₄-alkyl (eg. 1-methylcyclopropyl, 2,2-dimethylcyclopropyl or 1-methylcyclohexyl), C₁-C₄-alkoxy-C₁-C₄-alkyl (eg. methoxymethyl, ethoxymethyl, n- or isopropoxymethyl, n-, iso-, sec- or tert-butoxymethyl, 2-methoxyprop-2-yl, 2-ethoxyprop-2-yl, 2-n- or isopropoxyprop-2-yl or 2-n-, iso-, sec- or tert-butoxyprop-2-yl), C₁-C₄-alkylthio-C₁-C₄-alkyl (eg. methylthiomethyl, ethylthiomethyl, n- or isopropylthiomethyl, n-, iso-, sec- or tert-butylthiomethyl, 2-methylthioprop-2-yl, 2-ethylthioprop-2-yl, 2-n- or isopropylthioprop-2-yl or 2-n-, iso-, sec- or tert-butylthioprop-2-yl), aryl(phenyl)thio-C₁-C₄-alkyl (eg. phenylthiomethyl or 2-chlorophenylthiomethyl), C₂-C₆-alkenyl (eg. vinyl, 1-propenyl, 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 3-methyl-2-butenyl or 2-methyl-2-penten-5-yl), C₂-C₅-haloalkenyl (eg. 2,2-difluorovinyl, 2,2-dichlorovinyl, 3,3,3-trifluoropropenyl, 3,3,3-trichloropropenyl or 3-chloro-2-propenyl), C₃-C₆-cycloalkenyl (eg. cyclopent-1-enyl, cyclopentadienyl or cyclohex-1-enyl), C₃-C₆-halocycloalkenyl (eg. pentafluorocyclopentadienyl or pentachlorocyclopentadienyl), C₂-C₄-alkynyl (eg. ethnyl, 1-propynyl or 1-propargyl), C₁-C₄-alkoxy (eg. methoxy, ethoxy, n- or isopropoxy or n-, iso-, sec- or tert-butoxy), C₁-C₄-alkylthio (eg. methylthio, ethylthio, n- or isopropylthio or n-, iso-, sec- or tert-butylthio) or banzylthio, C₁-C₄-haloalkoxy (eg. trifluoromethoxy, pentafluoroethoxy or 1,1,2,2-tetrafluoroethoxy), N(R⁶)₂ (eg. amino, methylamino, dimethylamino, ethylamino, diethylamino, di-n-propylamino, diisopropylamino, di-n-butylamino or diisobutylamino), C₁-C₄-alkylcarbonyl (eg. acetyl, propionyl, butyryl, isobutyryl or pivaloyl), unsubstituted or substituted phenylcarbonyl (eg. benzoyl or 4-chlorobenzoyl), unsubstituted or substituted benzylcarbonyl (eg. benzylcarbonyl), C₁-C₄-alkoxycarbonyl (eg. methoxycarbonyl, ethoxycarbonyl, n- or isopropoxycarbonyl or n-, iso-, sec- or tertbutoxycarbonyl), unsubstituted or substituted phenoxycarbonyl (eg. phenoxycarbonyl or 4-chlorophenoxycarbonyl), unsubstituted or substituted benzyloxycarbonyl (eg. benzyloxycarbonyl), —CO—N(R⁷)₂ (eg. aminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, diisopropylaminocarbonyl, phenylaminocarbonyl or N-methyl-N-phenylaminocarbonyl), unsubstituted or substituted aryl (eg. phenyl, naphthyl or anthryl), unsubstituted or substituted aryloxy (eg. phenoxy, naphthyloxy or anthryloxy), unsubstituted or substituted arylthio (eg. phenylthio), unsubstituted or substituted aryl-C₁-C₄-alkyl (eg. benzyl, 1-phenethyl, 2-phenethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl, 2-methyl-3-phenylpropyl, 2-methyl-2-phenylpropyl or 4-phenylbutyl), unsubstituted or substituted aryl-C₁-C₄-alkenyl (eg. phenyl-1-etheny 1,2-phenyl-1-propenyl, 2,2-diphexylethenyl, 1-phenyl-1-propen-2-yl or 1-phenyl-1-ethenyl), unsubstituted or substituted aryloxy-C₁-C₄-alkyl (eg. phenoxymethyl), unsubstituted or substituted arylthio-C₁-C₄-alkyl (eg. phenylthiomethyl), unsubstituted or substituted hetaryl (eg. pyridyl; 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrimidinyl, 2,6-pyrimidinyl, 1,5-pyrimidinyl, thienyl, 2-thienyl, 3-thienyl, furyl, 2-furyl, 3-furyl, 1-pyrrolyl, 1-imidazolyl, 1,2,4-triazolyl, 1,3,4-triazolyl, 4-thiazolyl or 2-benzothiazolyl), unsubstituted or substituted hetaryloxy (eg. 2-pyridyloxy or 2-pyrimidinyloxy), unsubstituted or substituted hetarylthio (eg. 2-pyridylthio, 2-pyrimidinylthio or 2-benzothiazolylthio), unsubstituted or substituted hetaryl-C₁-C₄-alkyl (eg. 2-pyridylmethyl or 3-pyridylmethyl), unsubstituted or substituted hetaryloxy-C₁-C₄-alkyl (eg. furfurylmethoxy, thienylmethoxy, 3-isoxazolylmethoxy, 2-oxazolylmethoxy or 2-pyridylmethoxy), unsubstituted or substituted hetaryl-C₂-C₄-alkenyl (eg. 2′-furyl-2-ethenyl, 2′-thienyl-2-ethenyl or 3′-pyridyl-2-ethenyl), unsubstituted or substituted heterocyclyl (eg. oxiranyl, 1-aziridinyl, 1-azetidinyl, 1-pyrrolidinyl, 2-tetrahydrofuryl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 1-piperidinyl, 1-morpholinyl, 1-piperazinyl, 1,3-dioxanyl or 3-tetrahydrothiopyranyl) or unsubstituted or substituted heterocyclyloxy (eg. 2-dihydropyranyloxy or 2-tetrahydropyranyloxy).

The radicals referred to above in connection with unsubstituted or substituted are, in addition to hydrogen, for example, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, trifluoromethoxy,1,1,2,2-tetrafluoroethoxy, methoximinomethyl, ethoximinomethyl, n-propoximinomethyl, n-butoximinomethyl, n-pentyloximinomethyl, n-hexyloximinomethyl, allyloximinomethyl, benzyloximinomethyl, isopropoximinomethyl, isobutoximinomethyl, tert-butoximinomethyl, methylimino-1-ethyl, ethoximino-1-ethyl, n-propoximino-1-ethyl, n-butoximino-1-ethyl, n-pentyloximino-1-ethyl, n-hexyloximino-1-ethyl, allyloximino-1-ethyl, benzyloximino-1-ethyl, phenyl, phenoxy, benzyloxy, imidazol-1-yl, piperazin-1-yl, 4-morpholinyl, piperidin-1-yl, pyrid-2-yloxy, cyclopropyl, cyclohexyl, oxiranyl, 1,3-dioxan-2yl, 1,3-dioxolan-2-yl and tetrahydropyran-2-yloxy.

The group

may also be the radical of a carbocyclic or heterocyclic oxime (eg. cyclopentanone oxime, cyclohexanone oxime, cycloheptanone oxime, 2-adamantanone oxime, D-camphor oxime, 1-tetralone oxime, 1-indanone oxime, 9-fluorenone oxime, 1-methyl-4-piperidone oxime, violaric acid or N,N-dimethylvioluric acid).

R³ and R⁴ together then form, for example, a cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, camphenyl, tetralin, indane or fluorene ring.

One of the radicals R³ or R⁴ may furthermore be halogen (eg. fluorine, chlorine, bromine or iodine).

n may be 1, 2, 3 or 4 and R⁸ may be for example H, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, trifluoromethoxy, 1,1,2,2-tetrafluoromethoxy, phenyl, phenoxy, benzyloxy or pyrid-2-yl, where these radicals in turn may be substituted by fluorine, chlorine, bromine, iodine, cyano, methyl or methoxy.

Among the compounds in which R³ and R⁴ are hydrogen, the preferred compounds are those in which either only R³ or only R⁴ is hydrogen, in particular the compounds in which R³ is hydrogen.

Also preferred are compounds of the formula II in which X is CH₂, CHCH₃, CHC₂H₅, CHOCH₃, CHOC₂H₅, CHSCH₃ or CHSC₂H₅, Y is 0, R¹ is C₁-C₄-alkyl, R² is H or methyl, R³ and R⁴ are identical or different and each is hydrogen, cyano, straight-chain or branched C₁-C₁₀-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl, arylthio-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₂-C₄-haloalkenyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted aryl-C₁-C₄-alkyl, substituted or unsubstituted aryl-C₂-C₄-alkenyl, substituted or unsubstituted aryloxy-C₁-C₄-alkyl, substituted or unsubstituted hetaryl, substituted or unsubstituted hetaryloxy, substituted or unsubstituted hetarylthio or substituted or unsubstituted heterocyclyl, or each is N(R⁶)₂, R⁶ being identical or different and denoting H, C₁-C₆-alkyl, C₃-C₆-cycloalkyl or substituted or unsubstituted phenyl, or each is —CO—N(R⁷)₂, R⁷ being identical or different and denoting H or C₁-C₄-alkyl, the term “substituted” denoting the radicals listed in claim 1, and R³ and R⁴ may together denote a carbocyclic or heterocyclic ring which may be substituted by the radicals given under “substituted”, and R³ and R⁴ may be halogen, and Z¹ and Z² are hydrogen, fluorine, chlorine, bromine, iodine, methyl, cyano or methoxy.

Owing to the C═C or C═N double bonds, the novel compounds of the general formula I may be obtained in the preparation as E/Z isomer mixtures. These can be separated into the individual components in a conventional manner, for example by crystallization or chromatography.

Both the individual isomeric compounds and mixtures thereof form subjects of the invention and can be used a pesticides.

The compounds of the general formula I as claimed in claim 1 are prepared, for example, as described in Scheme 1 (Z¹ and Z² are each H).

The compounds of the general formula I in which X is CH₂, CH-alkyl or CH-alkoxy can be prepared, for example, from the ketoesters 4 by a Wittig or Wittig-Horner reaction (cf. European Patents 348,766 and 178,826 and DE 3 705 389). The similar compounds 5 are likewise obtained from the ketoesters 2.

Alternatively, it is also possible to adopt a procedure in which compounds of the formula 7 or 9 are condensed with suitable reagents, for example with formaldehyde where X is CH₂ (cf. DE 3317356), a) with aldehydes (cf. D. M. Brown, J. Chem. Soc. 1948, 2147) or b) first with N,N-dimethylformamide dimethyl acetal, followed by reaction with a Grignard reagent (similarly to C. Jutz, Chem. Ber. 91 (1958), 1867) where X is CH-alkyl, or with a formate followed by alkylation (cf. European Patent 178,826) where X is CH—O-alkyl. Further preparation methods for the compounds of the formula 5 and I where X is CH—O-alkyl are described in European Patent 178,826.

Another possible method for preparing the compounds of the formula I where X is CH-alkyl and YR₂ is COOAlk is to react ketene acetals with phenylchlorocarbenes (S. N. Slougui and G. Rousseau, Synth. Commun. 12 (5) (1982), 401-407).

For compounds of the general formula I where X is CH-S-alkyl, the preparation can be carried out by the methods described in European Patents 244077 or 310,954.

The intermediates of the formulae 3, 6 and 8 can be prepared from the compounds 2, 5 and 7 by halogenating the latter by a known method, for example with chlorine, bromine or N-bromosuccinimide, in an inert solvent (eg. CCl₄ or cyclohexane), with exposure to, for example, a Hg vapor lamp or in the presence of a free radical initiator, eg. dibenzoyl peroxide, or by introducing the radicals L, eg. mesylate, tosylate, acetate or triflate, via suitable intermediates (where L is halogen or OH).

The oxime ethers of the formula I where X is N-Oalkyl can be prepared from 4 a) by reaction with an O-alkylhydroxylamine hydrochloride or b) with hydroxylamine hydrochloride and subsequent alkylation with an alkylating agent (eg. an alkyl iodide, dialkyl sulfate, etc.) (cf. DE 3 623 921).

Furthermore, a phenylacetic ester of the formula 9 can be converted with a base (eg. NaOMe, NaH, K tert-butylate, etc.) in a solvent (eg. diethyl ether, toluene, tert-butanol, etc.) by a method similar to that in European Patent 254,426 into its anion and can be converted into the oxime with a suitable nitrosating agent (such as methyl nitrite, amyl nitrate, tert-butyl nitrate, etc.). The resulting oximate is alkylated with an alkylating agent (eg. an alkyl iodide or dialkyl sulfate).

The same processes can also be applied to the compounds of the formulae 2 and 7, and the resulting oxime ethers 5 can be converted in a known manner (European Patent 254,426) via the intermediates 6 (L is, for example, halogen) into the desired compounds I.

In the preparation processes described above, Y—R¹ is usually alkoxy.

The compounds in which YR¹ is OH (11) can be prepared by methods known from the literature (Organikum 16th edition, pages 415 and 622), from the compounds of the general formula I where YR¹ is COOAlkyl (10) (cf. Scheme 2):

Alternatively, the nitriles 12 can be converted in a known manner (cf. Organikum 16th edition, page 424 et seq. (1985) into the carboxylic acids 11.

The resulting carboxylic acids 11 can be converted in a conventional manner into the acyl chlorides 14 (cf. Organikum 16th edition, page 423 et seq. (1985). The conversion of 14 into the amides 15 is effected by methods similar to that described in Organikum 16th edition, page 412 (1985).

The thioesters 13 are obtained from the acyl chlorides 14 (similarly to Houben-Weyl Vol. 8, page 464 et seq. (1952)).

Alternatively, the thioesters 13 can also be prepared from the acids 11 (similarly to Houben-Weyl Vol. E5, page 855 et seq. (1985)).

The amides 15 in which R¹ and R⁵ are each H can also be prepared from the nitriles 12 by processes known from the literature (cf. Synthesis 1980, 243).

The preparation of the compounds of the general formulae 2 and 7 with ortho-methyl substitution at the aromatic (R²═H) is known.

(YR¹═OAlkyl; cf. European Patents 178,826 and 260,832).

The oximes required for the preparation of the compounds of the general formula I are either known or can be prepared by one of the processes shown in Scheme 3.

Methods for the conversion of 16 or 18 into 17 are described in Houben-Weyl, Vol. 10/4 (1968).

Furthermore, aldoximes 19 can be chlorinated by known methods and can be reacted with, for example, a cyanide to give the derivatives 17 (R⁴═CN) (cf. M. R. Zimmermann J. f. prakt. Chemie 66 (1902), 359).

The specific derivatives in which R³ is CN and R⁴ is alkoxyalkyl are prepared according to European Patent 74,047, those in which R³ is CN and R⁴ is alkylthioalkyl according to European Patent 150,822 and those in which R³ is CN and R⁴ is alkyl according to DE 2 304 848.

The method employing Me₃SiO—NH—SiMe₃ (R. U. Hoffmann and G. A. Buntain, Synthesis 1987, 831) is used for sterically hindered ketones.

The novel compounds of the general formula I as claimed in claim 1 are prepared, for example, by a method in which an oxime of the formula 17 is reacted with a substituted benzyl compound 6 in which L is a leaving group (eg. chloride, bromide, p-toluenesulfonate, methanesulfonate, triflate or acetate). R¹-R⁴, X and Y have the abovementioned meanings.

The reactions described can be carried out, for example, in an inert solvent (eg. acetone, acetonitrile, dimethyl sulfoxide, dimethylformamide, N-methylpyrrolidone or pyridine) with the use of a base (eg. sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, sodium hydride or sodium methylate).

The reactions can also be carried out in a two-phase system (eg. dichloromethane or water) with the aid of a suitable phase transfer catalyst (eg. cetyltrimethylammonium chloride or benzyltrimethylammonium chloride).

Another method for the preparation of compounds I (YR¹═OAlkyl, X═CH—OAlkyl or N—OAlkyl and L═Cl, Br, tosylate or mesylate) is illustrated by Scheme 5:

This synthesis sequence is carried out, as far as compound 22, similarly to the methods described in European Patent 244,786.

For example, N-hydroxyphthalimide can be converted with a halide or sulfonic ester 6 in the presence of an acid acceptor (eg. triethylamine, potassium carbonate, etc.), in a suitable solvent (eg. N-methylpyrrolidone, dimethylformamide, etc.), into the imidoether 21.

Cleavage to give the O-substituted hydroxylamine can be effected with a mineral acid (eg. HCl; cf. Houben-Weyl Vol. 10/1, page 1181 et seq.) or with a base (for example with hydrazine or ethanolamine).

The conversion of amine 22 to I is carried out in a conventional manner (cf. D. Otzanak, J. C. S. Chem. Commun. 1986, 903).

The Examples and methods which follow are intended to illustrate the preparation of the novel active ingredients and of the novel intermediates.

Method 1: 3,4-Dichloroacetophenone oxime

12.0 g (0.17 mol) of hydroxylammonium hydrochloride and 18.9 g (0.1 mol) of 3,4-dichloroacetophenone are added to a mixture of 20 ml of H₂O, 100 ml of methanol and 8 g (0.1 mol) of pyridine. Refluxing is carried out for 1 hour, after which the mixture is acidified with 2N HCl and extracted with 3×100 ml of tert-butyl methyl ether. The organic phase is washed with water, dried with Na₂SO₄ and evaporated down. 19.6 g (96% of theory) of crystals of melting point 92° C., which according to ¹H-NMR consist of 90% of trans-oxime, are obtained.

Method 2: 2-Oximino-2-tetrahydropyran-2′-ylacetonitrile

265.4 g (2.05 mol) of tetrahydrofuran-2-carbaldehyde oxime in 2 l of diethyl ether are initially taken at from −55° to −60° C. 153.5 g (2.15 mol) of chlorine are then passed in and the temperature is increased to −20° C.; stirring is carried out for 1 hour, the mixture is then evaporated down in a rotary evaporator at 10° C., the residue is taken up in 1.5 l of diethyl ether and the solution is stirred overnight in the absence of light, while cooling with ice. The solution is then filtered and the filtrate is added dropwise, while cooling with ice, to 147.3 g (2.27 mol) of potassium cyanide in 1 l of methanol at 10°-15° C. (exothermic). Stirring is carried out for 5 hours at room temperature (20° C.), after which the precipitate is filtered off under suction and washed twice with diethyl ether. The organic phases are partitioned between tert-butyl methyl ether and water and the residue of the ether phases is crystallized from dichloromethane/n-hexane at 0° C.

After filtration under suction and drying, 208 g (66% of theory) of a spectroscopically pure substance of melting point 105°-106° C. remain.

Method 3: 3-Methoxy-3-methyl-2-oximinobutyronitrile

53.6 g (0.46 mol) of 2-methoxy-2-methylpropionaldehyde oxime in ether (about 1M) are initially taken at from −5° to −10° C. 35.8 g (0.5 mol) of chlorine gas are passed in, after which stirring is carried out for 1 hour at this temperature and the mixture is then evaporated down at 10° C. and the residue is taken up in diethyl ether. 24.7 g (0.5 mol) of sodium cyanide in 375 ml of 20:1 methanol/H₂O are initially taken at 10° C. and the above ethereal solution is rapidly added dropwise. After 4 hours at room temperature, the mixture is filtered under suction and the residue is washed with twice 100 ml of methanol. The combined solutions are evaporated down and the residue is partitioned between methyl tert-butyl ether and water. Drying the organic phase over Na₂SO₄, evaporating down and crystallizing from dichloromethane/n-hexane give 41.1 g (63% of theory) of a white powder of melting point 102°-104° C.

Method 4:Methyl 3-methoxy-2-[2′-(phthalimido-oxy)-methyl]-phenylacrylate

10 g (35 mmol) of methyl 3-methoxy-2-(2′-bromomethyl)-phenylacrylate, 5.7 g (35 mmol) of hydroxyphthalimide, 3.9 g (38.6 mmol) of triethylamine and 50 ml of N-methylpyrrolidone are combined and the mixture is stirred for 2 hours at 60° C. It is then poured onto ice water, and the residue is filtered off under suction, washed with water and isopropanol and dried under reduced pressure. 9.0 g (70% of theory) of a crystalline product of melting point 156°-158° C. remain.

¹H-NMR (CDCl₃) δ=3.60 (s, 3H); 3.75 (s, 3H); 5.12 (s, 2H); 7.13 (dbr, 1H); 7.35 (m, 2H); 7.62 (s, 1H); 7.7-7.9 (m, 5H)

Method 5: Methyl 3-methoxy-2-(2′-aminooxymethyl)-phenylacrylate

10.0 g (27 mmol) of the product from Method 4 are dissolved in 150 ml of methanol and the solution is stirred with 1.4 g (27 mmol) of hydrazine hydrate for 2 hours at room temperature. The precipitate is filtered off under suction, the mother liquor is evaporated down, the residue is stirred with diethyl ether, the precipitate is filtered off under suction again and the mother liquor is evaporated down. 6.0 g (92% of theory) of a yellow oil result (purity according to ¹H-NMR about 90%).

¹H-NMR (CDCl₃) δ=3.71 (s, 3H); 3.80 (s, 3H); 4.60 (s, 2H); (5.35 (sbr, 2H); 7.0-7.50 (m, 4H); 7.58 (s, 1H).

Method 6: Methyl 2-methoximino-2-(2′-phthalimidooxymethyl)-phenylacetate

2.0 g (7 mmol) of methyl 2-methoximino-2-(2′-bromomethyl)-phenylacetate, 1.1 g (7 mmol) of hydroxyphthalimide and 0.8 g (7.7. mmol) of triethylamine are dissolved in 10 ml of N-methylpyrrolidone and the solution is stirred for 2 hours at 70° C. For working up, ice water is added, and the crystals are filtered off under suction, washed with water and methyl tert-butyl ether and dried.

1.5 g (58% of theory) of crystals of melting point 152°-155° C. remain.

¹H-NMR (CDCl₃) δ=3.83 (s, 3H); 3.98 (s, 3H); 5.07 (s, 2H); 7.15 (dbr, 1H); 7.45 (mc, 2H); 7.60-7.85 (m, 5H)

Method 7: Methyl 2-methoximino-2-(2′-aminooxymethyl)-phenylacetate

15.0 g (41 mmol) of the product from Method 6 are stirred with 2.1 g (42 mmol) of hydrazine hydrate in 150 ml of methanol for 2 hours at room temperature. The residue is again filtered off under suction, the mother liquor is evaporated down and triturated with diethyl ether, the residue is filtered off under suction and the mother liquor is evaporated down. 7.8 g (80% of theory) of an acid-sensitive oil remain.

¹H-NMR (CDCl₃): δ=3.90 (s, 3H); 4.03 (s, 3H); 4.59 (s, 2H); 5.35 (sbr, 2H); 7.15 (dbr, 1H); 7.40 (sbr, 3H)

EXAMPLE 1 Methyl 3-methoxy-2-[2′-[1″-(3′″,5′″-dichlorophenyl)-1″-methyl]-iminooxymethyl]-phenylacrylate (No. 582, Table I)

0.6 g (25 mmol) of sodium hydride powder in 100 ml of acetonitrile is initially taken, 5.1 g (25 mmol) of 3,5-dichloroacetophenone oxime are added and the mixture is refluxed for 1 hour. Thereafter, 9.3 g (33 mmol) of methyl 2-(2′-bromomethyl)-phenyl-3-methoxyacrylate in 50 continued for a further 4 hours. The mixture is evaporated down under reduced pressure and then partitioned between methyl tert-butyl ether and saturated ammonium chloride solution, the organic phase is washed with water and the residue obtained by evaporation is crystallized from methyl butyl ether/n-hexane. 4.6 g (45% of theory) of a substance of melting point 87°-88° C. are obtained.

¹H-NMR (CDCl₃): δ=2.19 (s, 3H); 3.70 (s, 3H); 3.81 (s, 3H); 5.15 (s, 2H); 7.08 (m, 1H); 7.17 (m, 3H); 7.50 (m, 3H); 7.58 (s, 1H)

EXAMPLE 2 Methyl 3-methoxy-2-[2′-(1″-cyano-(-1″-methoxy-1″-methylethyl)-imminooxymethyl]-phenylacrylate (No. 36, Table I)

3.3 g (23 mmol) of 3-methoxy-3-methyl-2-oximinobutyronitrile, 6.6 g (23 mmol) of methyl 2-(2′-bromomethylphenyl)-3-methoxyacrylate and 3.2 g (23 mmol) of potassium carbonate in 60 ml of N,N-dimethylformamide are stirred for 15 hours at room temperature. The mixture is then evaporated down, the residue is taken up in ethyl acetate, the solution is washed with 3×50 ml of water and the organic phase is dried over sodium sulfate, evaporated down and chromatographed over silica gel using 40:1 toluene/ethyl acetate.

Yield: 7.0 g (88% of theory) of an oil.

IR (film): 1,285, 1,258, 1,189, 1,180, 1,131, 1,111, 1,069, 1,008 cm⁻¹.

EXAMPLE 3 Methyl 2-methoximino-2-[2′-(1″-(3′″,5′″-dichlorophenyl)-1″-methyl)-iminooxymethyl]-phenylacetate (No. 582, Table II)

0.6 g (25 mmol) of NaH in 50 ml of acetonitrile is initially taken, and 5.1 g (25 mmol) of 3,5-dichloroacetophenone oxime are added at room temperature. Refluxing is carried out for 1 hour, after which 9.4 g (33 mmol) of methyl 2-methoximino-2-(2′-bromomethyl)-phenylacetate in 50 ml of acetonitrile are added dropwise and refluxing is continued for a further 4 hours. After evaporating down, partitioning the residue between water/methyl tert-butyl ether, washing the organic phase with water, drying the organic phase with sodium sulfate and evaporating down, the residue is subjected to column chromatography over silica gel using methyl tert-butyl ether/hexane, 5.4 g (53% of theory) of crystals of melting point 95°-97° C. result.

¹H-NMR (CDCl₃): δ=2.17 (s, 3H); 3.82 (s, 3H); 4.02 (s, 3H); 5.15 (s, 2H); 7.20 (dbr, 1H); 7.25-7.55 (m, 6H)

EXAMPLE 4 Methyl 3-methoxy-2-[2′-(1″-(4′″-bromophenyl)-1″-methyl)-iminooxymethyl]-phenylacrylate (No. 593, Table I)

2.37 g (10 mmol) of methyl 3-methoxy-2-(2′-aminooxymethyl)-phenylacrylate, 1.99 g (10 mmol) of 4-bromoacetophenone, 2 ml of water, 0.8 g of pyridine and 10 ml of methanol are combined and the mixture is stirred for 24 hours at room temperature. The mixture is evaporated down, the residue is partitioned between water/methyl tert-butyl ether and the organic phase is washed with 2N HCl and washed neutral with NaH—CO₃ and evaporated down, and the residue is chromatographed over SiO₂ using methyl tert-butyl ether/hexane. 2.1 g (51% of theory) of crystals of melting point 105°-107° C. result.

¹H-NMR (CDCl₃): δ=2.22 (s, 3H); 3.70 (s, 3H); 3.80 (s, 3H); 5.15 (s, 2H); 7.16 (dbr, 1H); 7.33 (m, 2H); 7.45 (m, 5H); 7.58 (s, 1H)

EXAMPLE 5 Methyl 2-methoximino-2-[2′-(1″-(4′″-nitrophenyl)-1″-methyl)-iminooxymethyl]-phenylacetate (No. 614, Table II)

2.38 g (10 mmol) of methyl 2-methoximino-2-(2′-aminooxymethyl)-phenylacetate, 1.65 g (10 mmol) of 4-nitroacetophenone, 2 ml of water, 0.8 g of pyridine and 10 ml of methanol are reacted as in Example 4. 2.1 g (55% of theory) of crystals of melting point 87°-89° C. are obtained.

¹H-NMR (CDCl₃): δ=2.22 (s, 3H); 3.81 (s, 3H); 4.02 (s, 3H); 5.18 (s, 2H); 7.20 (dd, 1H); 7.4 (m, 3H); 7.75 (dd, 2H); 8.18 (dd, 2H).

EXAMPLE 6 Methyl 3-methoxy-2-[2′-(1″-(4′″-chlorophenyl)-iminooxymethyl]-phenylacrylate (No. 95 Table 5)

a) 5.5 g (15 mmol) of methyl 3-methoxy-2-[2′-(phthalimidooxy)-methyl]-phenylacrylate (from Method 4) in 100 ml of methanol are initially taken, and 0.75 g (15 mmol) of hydrazine hydrate is added at room temperature. After 15 minutes at this temperature, the mixture is evaporated down, the residue is triturated with methyl tert-butyl ether and the cleavage product is filtered off under suction. The mother liquor is evaporated down, the residue is taken up with 50 ml of methanol and 2.1 g (15 mmol) of 4-chlorobenzaldehyde in 50 ml of methanol plus 1 drop of pyridine are added dropwise.

Stirring was carried out overnight at 23° C., after which the product was filtered off under suction, washed with methanol and dried.

2.9 g (54% of theory) of crystals of melting point 87°-89° C. were obtained.

¹H-NMR (CDCl₃): δ=3.66 (s, 3H); 3.80 (s, 3H); 5.13 (s, 2H); 7.17 (m, 1H); 7.35 (m, 4H); 7.50 (me, 3H); 7.60 (s, 1H); 8.06 (s, 1H).

b) 50 ml of methanol are slowly added to 1.3 g (55 mmol) of NaH powder under a nitrogen atmosphere (evolution of hydrogen). 7.8 g (50 mmol) of 4-chlorobenzaldehyde oxime in 50 ml of methanol are then added at room temperature. Stirring is carried out for half an hour, after which 14.3 g (50 mmol) of methyl 3-methoxy-2-(2′-bromomethyl)-phenylacrylate in 50 ml of methanol are added dropwise and stirring is carried out at room temperature for a further 48 hours. The white residue is filtered off under suction, washed with methanol and dried. 1.9 g (11% of theory) of a product of melting point 82°-84° C. are obtained.

EXAMPLE 7 Methyl 2-methoximino-2-(2′-phthalimidooxymethyl)-phenylacetate (No. 1, Table 8)

2.0 g (7 mmol) of methyl 2-methoxyimino-2-(2′-bromomethyl)-phenylacetate, 1.1 g (7 mmol) of hydroxyphthalimide and 0.8 g (7.7 mmol) of triethylamine are dissolved in 10 ml of N-methylpyrrolidone and the mixture is stirred for 2 hours at 70° C. Ice water is added and the crystals are filtered off under suction, washed with water and methyl tert-butyl ether and dried. There remain 1.5 g (58% of theory) of crystals of melting point 152°-155° C.

¹H-NMR (CDCl₃): δ=3.83 (s, 3H); 3.98 (s, 3H); 5.07 (s, 2H); 7.15 (dbr, 1H); 7.45 (mc, 2H); 7.60-7.85 (m, 5H).

The compounds listed in Tables I-IX can be prepared in a similar manner.

TABLE I

No. R³ R⁴ Data  1 Cl Phenyl  2 Cl Cyano  3 Cl Ethoxycarbonyl  4 Cl Cyclopropyl  5 CF₃ CF₃  6 CF₃ Phenyl  7 CCl₃ CCl₃  8 CCl₃ Phenyl  9 CH₂Cl Phenyl  10 CH₂CF₃ Phenyl  11 CF₂Cl Phenyl  12 CHCl₂ Phenyl  13 Cyclopropyl Cyclopropyl  14 Cyclopropyl Phenyl oil; IR (film): 1190, 1129, 1056, 1032, 768  15 Cyclopropyl 4-Fluorophenyl oil; IR (film): 1508, 1225, 1129, 998, 839  16 Cyclopropyl 4-Chlorophenyl oil; IR (film): 1490, 1129, 1091, 1014, 1800  17 Cyclopropyl 4-Methoxyphenyl oil; IR (film): 1251, 1177, 1129, 1033  18 Cyclopropyl 4-Ethoxyphenyl  19 Cyclopropyl 4-Phenoxyphenyl  20 Cyclopropyl Pentachlorophenyl  21 Cyclopropyl Pentafluorophenyl  22 Cyclopentyl Phenyl  23 Cyclohexyl Phenyl  24 Phenyl 2,2-Dichloro-1-methylcyclopropyl  25 Phenyl 2,2-Difluorocyclopropyl  26 Phenyl 2,2-Dichlorocyclopropyl  27 Phenyl 2,2-Dibromocyclopropyl  28 Phenyl 2,2,3,3-Tetrafluorocyclobutyl  29 Phenyl 2,2-Dimethylcyclopropyl  30 Phenyl 1-Methylcyclohexyl  31 CN Methoxymethyl  32 CN Ethoxymethyl  33 CN n-Propoxymethyl  34 CN iso-Propoxymethyl  35 CN tert.-Butoxymethyl  36 CN 2-Methoxyprop-2-yl oil; IR (film): 1436, 1191, 1131, 1057, 1003  37 CN 2-Ethoxyprop-2-yl oil; IR (film): 1191, 1177, 1131, 1095, 1010  38 CN 2-n-Propoxyprop-2-yl oil; IR (film): 1191, 1175, 1131, 1060, 1005  39 CN 2-iso-Propoxyprop-2-yl oil; IR (film): 1370, 1191, 1172, 1131, 998  40 CN 2-tert.-Butoxyprop-2-yl  41 CN Methylthiomethyl  42 CN tert.-Butylthiomethyl  43 CN 2-Methylthioprop-2-yl oil; IR (film): 1436, 1191, 1131, 1114, 1086, 998  44 CN 2-iso-Propylthioprop-2-yl  45 CN 2-tert.-Butylthioprop-2-yl oil; IR (film): 1366, 1191, 1132, 1113, 1012, 1000  46 CN Methyl  47 CN Ethyl  48 CN n-Propyl  49 CN iso-Propyl oil; IR (film): 1285, 1258, 1189, 1131, 1111, 1069, 1006  50 CN n-Butyl  51 CN iso-Butyl  52 CN sec.-Butyl  53 CN tert.-Butyl  54 CN n-Hexyl  55 CN n-Decyl  56 CN Cyclopropyl oil; IR (film): 1207, 1190, 1130, 1057, 1003  57 CN Cyclohexyl  58 CN Phenylthiomethyl  59 CN 2-Phenylthiomethyl  60 CN 2-(2′-Chlorophenylthio)prop-2-yl  61 CN Ethynyl  62 CN 1-Propynyl  63 CN Methoxy  64 CN Ethoxy  65 CN n-Propoxy  66 CN iso-Propoxy  67 CN n-Butoxy  68 CN iso-Butoxy  69 CN sec.-Butoxy  70 CN tert.-Butoxy  71 CN Methylthio  72 CN Ethylthio  73 CN n-Propylthio  74 CN iso-Propylthio  75 CN n-Butylthio  76 CN iso-Butylthio  77 CN sec.-Butylthio  78 CN tert.-Butylthio  79 CN Benzylthio  80 CN Trifluoromethoxy  81 CN Cyano  82 CN Amino  83 CN Methylamino  84 CN Dimethylamino  85 CN Ethylamino  86 CN Diethylamino  87 CN Di-n-Propylamino  88 CN Di-iso-Propylamino  89 CN Di-n-Butylamino  90 CN Di-iso-Butylamino  91 CN Acetyl  92 CN Propion-1-yl  93 CN Butyr-1-yl  94 CN iso-Butyr-1-yl  95 CN Pivaloyl  96 CN Benzoyl  97 CN 4-Chlorobenzoyl  98 CN Benzylcarbonyl  99 CN Methoxycarbonyl 100 CN Ethoxycarbonyl 101 CN n-Propoxycarbonyl 102 CN iso-Propoxycarbonyl 103 CN n-Butoxycarbonyl 104 CN iso-Butoxycarbonyl 105 CN sec.-Butoxycarbonyl 106 CN tert.-Butoxycarbonyl 107 CN n-Hexoxycarbonyl 108 CN Phenoxycarbonyl 109 CN 4-Chlorophenoxycarbonyl 110 CN Benzyloxycarbonyl 111 CN Aminocarbonyl 112 CN Dimethylaminocarbonyl 113 CN Diethylaminocarbonyl 114 CN Di-iso-Propylaminocarbonyl 115 CN Phenylaminocarbonyl 116 CN N-Methyl-N-Phenylaminocarbonyl 117 CN Phenyl oil; IR (film): 1245, 1127, 1024, 1015, 767, 750 118 CN 2-Fluorophenyl 119 CN 3-Fluorophenyl 120 CN 4-Fluorophenyl 121 CN Pentafluorophenyl 122 CN 2-Chlorophenyl 123 CN 3-Chlorophenyl 124 CN 4-Chlorophenyl 125 CN Pentachlorophenyl 126 CN 2,3-Dichlorophenyl 127 CN 2,4-Dichlorophenyl 128 CN 2,5-Dichlorophenyl 129 CN 2,6-Dichlorophenyl 130 CN 3,4-Dichlorophenyl 131 CN 3,5-Dichlorophenyl 132 CN 2,3,4-Trichlorophenyl 133 CN 2,3,5-Trichlorophenyl 134 CN 2,3,6-Trichlorophenyl 135 CN 2,4,5-Trichlorophenyl 136 CN 2,4,6-Trichlorophenyl 137 CN 3,4,5-Trichlorophenyl 138 CN 2,3,4,6-Tetrachlorophenyl 139 CN 2,3,5,6-Tetrachlorophenyl 140 CN 2-Bromophenyl 141 CN 3-Bromophenyl 142 CN 4-Bromophenyl 143 CN 2,4-Dibromophenyl 144 CN 3-Bromo-4-fluorophenyl 145 CN 3-Bromo-4-methoxyphenyl 146 CN 2-Iodophenyl 147 CN 3-Iodophenyl 148 CN 4-Iodophenyl 149 CN 2-Chloro-4-fluorophenyl 150 CN 2-Chloro-5-fluorophenyl 151 CN 2-Chloro-6-fluorophenyl 152 CN 2-Chloro-4-bromophenyl 153 CN 2-Bromo-4-chlorophenyl 154 CN 2-Bromo-4-fluorophenyl 155 CN 3-Bromo-4-chlorophenyl 156 CN 3-Chloro-4-fluorophenyl 157 CN 3-Fluoro-4-chlorophenyl 158 CN 2-Cyanophenyl 159 CN 3-Cyanophenyl 160 CN 4-Cyanophenyl 161 CN 2-Nitrophenyl 162 CN 3-Nitrophenyl 163 CN 4-Nitrophenyl 164 CN 2-Methylphenyl 165 CN 3-Methylphenyl 166 CN 4-Methylphenyl 167 CN 2,4-Dimethylphenyl 168 CN 2,6-Dimethylphenyl 169 CN 3,4-Dimethylphenyl 170 CN 3,5-Dimethylphenyl 171 CN 2,3,4-Trimethylphenyl 172 CN 2,3,5-Trimethylphenyl 173 CN 2,3,6-Trimethylphenyl 174 CN 2,4,5-Trimethylphenyl 175 CN 2,4,6-Trimethylphenyl 176 CN 3,4,5-Trimethylphenyl 177 CN Pentamethylphenyl 178 CN 2-Ethylphenyl 179 CN 3-Ethylphenyl 180 CN 4-Ethylphenyl 181 CN 3,5-Diethylphenyl 182 CN 2-n-Propylphenyl 183 CN 3-n-Propylphenyl 184 CN 4-n-Propylphenyl 185 CN 2-iso-Propylphenyl 186 CN 3-iso-Propylphenyl 187 CN 4-iso-Propylphenyl 188 CN 2,4-Di-iso-Propylphenyl 189 CN 3,5-Di-iso-Propylphenyl 190 CN 4-n-Butylphenyl 191 CN 4-sec.-Butylphenyl 192 CN 4-iso-Butylphenyl 193 CN 4-tert.-Butylphenyl 194 CN 3-tert.-Butylphenyl 195 CN 2-tert.-Butylphenyl 196 CN 2,4-Di-tert.-Butylphenyl 197 CN 3,5-Di-tert.-Butylphenyl 198 CN 4-n-Hexylphenyl 199 CN 4-n-Dodecylphenyl 200 CN 2-Methyl-4-tert.-Butylphenyl 201 CN 2-Methyl-6-tert.-Butylphenyl 202 CN 2-Methyl-4-iso-Propylphenyl 203 CN 2-Methyl-4-Cyclophexylphenyl 204 CN 2-Methyl-4-Phenylphenyl 205 CN 2-Methyl-4-Benzylphenyl 206 CN 2-Methyl-4-Phenoxyphenyl 207 CN 2-Methyl-4-Benzyloxyphenyl 208 CN 2-Methyl-3-Chlorophenyl 209 CN 2-Methyl-4-Chlorophenyl 210 CN 2-Methyl-5-Chlorophenyl 211 CN 2-Methyl-6-Chlorophenyl 212 CN 2-Methyl-4-Fluorophenyl 213 CN 2-Methyl-3-Bromophenyl 214 CN 2-Methyl-4-Bromophenyl 215 CN 2-Methyl-3-Methoxyphenyl 216 CN 2-Methyl-4-Methoxyphenyl 217 CN 2-Methyl-5-methoxyphenyl 218 CN 2-Methyl-6-methoxyphenyl 219 CN 2-Methyl-4-iso-Propoxyphenyl 220 CN 2-Methyl-2,5-dimethoxyphenyl 221 CN 2-Methoxyphenyl 222 CN 3-Methoxyphenyl 223 CN 4-Methoxyphenyl 224 CN 2,3-Dimethoxyphenyl 225 CN 2,4-Dimethoxyphenyl 226 CN 2,5-Dimethoxyphenyl 227 CN 2,6-Dimethoxyphenyl 228 CN 3,4-Dimethoxyphenyl 229 CN 3,5-Dimethoxyphenyl 230 CN 3,6-Dimethoxyphenyl 231 CN 2,3,4-Trimethoxyphenyl 232 CN 2,3,5-Trimethoxyphenyl 233 CN 2,3,6-Trimethoxyphenyl 234 CN 2,4,5-Trimethoxyphenyl 235 CN 2,4,6-Trimethoxyphenyl 236 CN 3,4,5-Trimethoxyphenyl 237 CN 2-Ethoxyphenyl 238 CN 3-Ethoxyphenyl 239 CN 4-Ethoxyphenyl 240 CN 2-iso-Propoxyphenyl 241 CN 3-iso-Propoxyphenyl 242 CN 4-iso-Propoxyphenyl 243 CN 3-tert.-Butoxyphenyl 244 CN 4-tert.-Butoxyphenyl 245 CN 2-Trifluoromethoxyphenyl 246 CN 3-Trifluoromethoxyphenyl 247 CN 4-Trifluoromethoxyphenyl 248 CN 3-(1′,1′,2′,2′-Tetrafluoro)ethoxyphenyl 249 CN 4-(1′,1′,2′,2′-Tetrafluoro)ethoxyphenyl 250 CN 2-Chloromethylphenyl 251 CN 3-Chloromethylphenyl 252 CN 4-Chloromethylphenyl 253 CN 2-Trifluoromethylphenyl 254 CN 3-Trifluoromethylphenyl 255 CN 4-Trifluoromethylphenyl 256 CN 2-(Methoxyiminomethyl)phenyl 257 CN 3-(Methoxyiminomethyl)phenyl 258 CN 4-(Methoxyiminomethyl)phenyl 259 CN 2-(Ethoxyiminomethyl)phenyl 260 CN 3-(Ethoxyiminomethyl)phenyl 261 CN 4-(Ethoxyiminomethyl)phenyl 262 CN 2-(n-Propoxyiminomethyl)phenyl 263 CN 3-(n-Propoxyiminomethyl)phenyl 264 CN 4-(n-Propoxyiminomethyl)phenyl 265 CN 2-(iso-Propoxyiminomethyl)phenyl 266 CN 3-(iso-Propoxyiminomethyl)phenyl 267 CN 4-(iso-Propoxyiminomethyl)phenyl 268 CN 2-(n-Butoxyiminomethyl)phenyl 269 CN 3-(n-Butoxyiminomethyl)phenyl 270 CN 4-(n-Butoxyiminomethyl)phenyl 271 CN 2-(iso-Butoxyiminomethyl)phenyl 272 CN 3-(iso-Butoxyiminomethyl)phenyl 273 CN 4-(iso-Butoxyiminomethyl)phenyl 274 CN 2-(tert.-Butoxyiminomethyl)phenyl 275 CN 3-(tert.-Butoxyiminomethyl)phenyl 276 CN 4-(tert.-Butoxyiminomethyl)phenyl 277 CN 2-(n-Pentoxyiminomethyl)phenyl 278 CN 3-(n-Pentoxyiminomethyl)phenyl 279 CN 4-(n-Pentoxyiminomethyl)phenyl 280 CN 2-(n-Hexoxyiminomethyl)phenyl 281 CN 3-(n-Hexoxyiminomethyl)phenyl 282 CN 4-(n-Hexoxyiminomethyl)phenyl 283 CN 2-(Allyloxyiminomethyl)phenyl 284 CN 3-(Allyloxyiminomethyl)phenyl 285 CN 4-(Allyloxyiminomethyl)phenyl 286 CN 2-(Benzyloxyiminomethyl)phenyl 287 CN 3-(Benzyloxyiminomethyl)phenyl 288 CN 4-(Benzyloxyiminomethyl)phenyl 289 CN 2-(Methoxyimino-1′-ethyl)phenyl 290 CN 3-(Methoxyimino-1′-ethyl)phenyl 291 CN 4-(Methoxyimino-1′-ethyl)phenyl 292 CN 2-(Ethoxyimino-1′-ethyl)phenyl 293 CN 3-(Ethoxyimino-1′-ethyl)phenyl 294 CN 4-(Ethoxyimino-1′-ethyl)phenyl 295 CN 2-(n-Propoxyimino-1′-ethyl)phenyl 296 CN 3-(n-Propoxyimino-1′-ethyl)phenyl 297 CN 4-(n-Propoxyimino-1′-ethyl)phenyl 298 CN 2-(n-Butoxyimino-1′-ethyl)phenyl 299 CN 3-(n-Butoxyimino-1′-ethyl)phenyl 300 CN 4-(n-Butoxyimino-1′-ethyl)phenyl 301 CN 2-(n-Pentoxyimino-1′-ethyl)phenyl 302 CN 3-(n-Pentoxyimino-1′-ethyl)phenyl 303 CN 4-(n-Pentoxyimino-1′-ethyl)phenyl 304 CN 2-(n-Hexoxyimino-1′-ethyl)phenyl 305 CN 3-(n-Hexoxyimino-1′-ethyl)phenyl 306 CN 4-(n-Hexoxyimino-1′-ethyl)phenyl 307 CN 2-(Allyloxyimino-1′-ethyl)phenyl 308 CN 3-(Allyloxyimino-1′-ethyl)phenyl 309 CN 4-(Allyloxyimino-1′-ethyl)phenyl 310 CN 2-(Benzyloxyimino-1′-ethyl)phenyl 311 CN 3-(Benzyloxyimino-1′-ethyl)phenyl 312 CN 4-(Benzyloxyimino-1′-ethyl)phenyl 313 CN 2-Phenylphenyl 314 CN 3-Phenylphenyl 315 CN 4-Phenylphenyl 316 CN 2-Phenoxyphenyl 317 CN 3-Phenoxyphenyl 318 CN 4-Phenoxyphenyl 319 CN 2-Benzyloxyphenyl 320 CN 3-Benzyloxyphenyl 321 CN 4-Benzyloxyphenyl 322 CN 4-(Imidazol-1′-yl)phenyl 323 CN 4-(Piperazin-1′-yl)phenyl 324 CN 4-(Morpholin-1′-yl)phenyl 325 CN 4-(Piperidin-1′-yl)phenyl 326 CN 4-(Pyridyl-2′-oxy)phenyl 327 CN 2-Cyclopropylphenyl 328 CN 3-Cyclopropylphenyl 329 CN 4-Cyclopropylphenyl 330 CN 3-Cyclohexylphenyl 331 CN 4-Cyclohexylphenyl 332 CN 4-Oxiranylphenyl 333 CN 4-(1′,3′-Diozan-2′-yl)phenyl 334 CN 4-(Tetrahydropyran-2-yloxy)phenyl 335 CN 1-Naphthyl 336 CN 2-Naphthyl 337 CN 9-Anthryl 338 CN 1-Naphtoxy 339 CN 2-Naphtoxy 340 CN 9-Anthroxy 341 CN Phenoxy 342 CN 2-Chlorophenoxy 343 CN 3-Chlorophenoxy 344 CN 4-Chlorophenoxy 345 CN 4-Methylphenoxy 346 CN 4-tert.-Butylphenoxy 347 CN 4-Methoxyphenoxy 348 CN 4-Ethoxyphenoxy 349 CN 4-tert.-Butoxyphenoxy 350 CN Phenylthio 351 CN 2-Chlorophenylthio 352 CN 4-Chlorophenylthio 353 CN Benzyl 354 CN 2-Methylbenzyl 355 CN 3-Methylbenzyl 356 CN 4-Methylbenzyl 357 CN 4-tert.-Butylbenzyl 358 CN 2-Chlorobenzyl 359 CN 3-Chlorobenzyl 360 CN 4-Chlorobenzyl 361 CN 2,4-Dichlorobenzyl 362 CN 2,6-Dichlorobenzyl 363 CN 2,4,6-Trichlorobenzyl 364 CN 2-Trifluoromethylbenzyl 365 CN 3-Trifluoromethylbenzyl 366 CN 4-Trifluoromethylbenzyl 367 CN 2-Methoxybenzyl 368 CN 4-Methoxybenzyl 369 CN 4-tert.-Butoxybenzyl 370 CN 4-Phenoxybenzyl 371 CN 1-Phenethyl 372 CN 2-Phenethyl 373 CN 1-Phenylpropyl 374 CN 2-Phenylpropyl 375 CN 3-Phenylpropyl 376 CN 2-Methyl-2-phenylpropyl 377 CN 2-Methyl-3-phenylpropyl 378 CN 4-Phenylbutyl 379 CN 2-Phenyl-1-ethenyl 380 CN 1-Phenyl-1-ethenyl 381 CN 1-Phenyl-1-propenyl 382 CN 1-Phenyl-1-propen-2-yl 383 CN 2,2-Diphenylethenyl 384 CN Phenoxymethyl 385 CN 2-Pyridyl 386 CN 3-Pyridyl 387 CN 4-Pyridyl 388 CN 2,6-Pyrimidinyl 389 CN 1,5-Pyrimidinyl 390 CN 2-Thienyl 391 CN 3-Thienyl 392 CN 2-Furyl 393 CN 3-Furyl 394 CN 1-Pyrrolyl 395 CN 1-Imidazolyl 396 CN 1,2,4-Triazolyl 397 CN 1,3,4-Triazolyl 398 CN 4-Thiazolyl 399 CN 2-Benzothiazolyl 400 CN 2-Pyridyloxy 401 CN 2-Pyrimidinyloxy 402 CN 2-Pyridylthio 403 CN 2-Pyrimidinylthio 404 CN 2-Benzothiazolylthio 405 CN Phenylthiomethyl 406 CN 2-Pyridylmethyl 407 CN 3-Pyridylmethyl 408 CN Furfuryloxy 409 CN Thienylmethoxy 410 CN 3-Isoxazolylmethoxy 411 CN 2-Oxazolylmethoxy 412 CN 2-Pyridylmethoxy 413 CN 2′-Furyl-2-ethenyl 414 CN 2′-Thienyl-2-ethenyl 415 CN 3′-Pyridyl-2-ethenyl 416 CN Oxiranyl 417 CN 1-Aziridinyl 418 CN 1-Azetidinyl 419 CN 1-Pyrrolidinyl 420 CN 2-Tetrahydrofuryl 421 CN 2-Tetrahydropyranyl 422 CN 3-Tetrahydropyranyl 423 CN 1-Piperidinyl 424 CN 1-Morpholinyl 425 CN 1-Piperazinyl 426 CN 1,3-Dioxan-2-yl 427 CN 3-Tetrahydrothiopyranyl 428 CN 2-Dihydropyranyloxy 429 CN 2-Tetrahydropyranyloxy oil; IR (film): 1205, 1131, 1087, 1047, 1004 430 CN (CH₂)₄ 431 CN (CH₂)₅ 432 CN (CH₂)₆ 433 CN 434 CN 435 CN

436 CN

437 CN

438 CN

439 CN

440 CN

441 CN CF₃ 442 CN 2-Fluoroethyl 443 CN 2,2,2-Trifluoroethyl 444 CN Pentafluoroethyl 445 CN Chloromethyl 446 CN Dichloromethyl 447 CN Trichloromethyl 448 CN 2-Chloroethyl 449 CN 2,2,2-Trichloroethyl 450 CN Pentachloroethyl 451 CN Cyclopropyl 452 CN Cyclobutyl 453 CN Cyclopentyl 454 CN Cyclohexyl 455 CN 1-Methylcyclopropyl 456 CN 2,2-Dimethylcyclopropyl 457 CN 1-Methylcyclohexyl 458 CN 2,2-Difluorocyclopropyl 459 CN 2,2-Dichlorocyclopropyl 460 CN 2,2-Dibromocyclopropyl 461 CN 2,2-Dichloro-3-methylcyclopropyl 462 CN 2,2,3,3-Tetrafluorocyclopropyl 463 CN Ethenyl 464 CN 1-Propenyl 465 CN 2-Methyl-1-propenyl 466 CN 4-Methylpent-3-en-1-yl 467 CN 2-Propenyl 468 CN 2-Butenyl 469 CN 1-Methyl-2-propenyl 470 CN 3-Methyl-2-butenyl 471 CN 2,2-Difluoroenthenyl 472 CN 2,2-Dichloroenthenyl 473 CN 3,3,3-Trifluoropropenyl 474 CN 3,3,3-Trichloropropenyl 475 CN 3-Chloro-2-propenyl 476 CN Cyclopent-1-enyl 477 CN Cyclopentadienyl 478 CN Cyclohex-1-enyl 479 CN Pentafluorocyclopentadienyl 480 CN Pentachlorocyclopentadienyl 481 CN Styryl 482 CH₃ Methoxymethyl 483 CH₃ Ethoxymethyl 484 CH₃ n-Propoxymethyl 485 CH₃ iso-Propoxymethyl 486 CH₃ tert.-Butoxymethyl 487 CH₃ 2-Methoxyprop-2-yl 488 CH₃ 2-Ethoxyprop-2-yl 489 CH₃ 2-n-Propoxyprop-2-yl 490 CH₃ 2-iso-Propoxyprop-2-yl 491 CH₃ 2-tert.-Butoxyprop-2-yl 492 CH₃ Methylthiomethyl 493 CH₃ tert.-Butylthiomethyl 494 CH₃ 2-Methylthioprop-2-yl 495 CH₃ 2-iso-Propylthioprop-2-yl 496 CH₃ 2-tert.-Butylthioprop-2-yl 497 CH₃ Methyl 498 CH₃ Ethyl 499 CH₃ n-Propyl 500 CH₃ iso-Propyl 501 CH₃ n-Butyl 502 CH₃ iso-Butyl 503 CH₃ sec.-Butyl 504 CH₃ tert.-Butyl 505 CH₃ n-Hexyl 506 CH₃ n-Decyl 507 CH₃ Cyclopropyl 508 CH₃ Cyclohexyl 509 CH₃ Phenylthiomethyl 510 CH₃ 2-Phenylthiomethyl 511 CH₃ 2-(2′-Chlorophenylthio)prop-2-yl 512 CH₃ Ethenyl 513 CH₃ 1-Propynyl 514 CH₃ Methoxy 515 CH₃ Ethoxy 516 CH₃ n-Propoxy 517 CH₃ iso-Propoxy 518 CH₃ n-Butoxy 519 CH₃ iso-Butoxy 520 CH₃ sec.-Butoxy 521 CH₃ tert.-Butoxy 522 CH₃ Methylthio 523 CH₃ Ethylthio 524 CH₃ n-Propylthio 525 CH₃ iso-Propylthio 526 CH₃ n-Butylthio 527 CH₃ iso-Butylthio 528 CH₃ sec.-Butylthio 529 CH₃ tert.-Butylthio 530 CH₃ Benzylthio 531 CH₃ Trifluoromethoxy 532 CH₃ Cyano 533 CH₃ Amino 534 CH₃ Methylamino 535 CH₃ Dimethylamino 536 CH₃ Ethylamino 537 CH₃ Diethylamino 538 CH₃ Di-n-Propylamino 539 CH₃ Di-iso-Propylamino 540 CH₃ Di-n-Butylamino 541 CH₃ Di-iso-Butylamino 542 CH₃ Acetyl 543 CH₃ Propion-1-yl 544 CH₃ Butyr-1-yl 545 CH₃ iso-Butyr-1-yl 546 CH₃ Pivaloyl 547 CH₃ Benzoyl 548 CH₃ 4-Chlorobenzoyl 549 CH₃ Benzoylcarbonyl 550 CH₃ Methoxycarbonyl 551 CH₃ Ethoxycarbonyl 552 CH₃ n-Propoxycarbonyl 553 CH₃ iso-Propoxycarbonyl 554 CH₃ n-Butoxycarbonyl 555 CH₃ iso-Butoxycarbonyl 556 CH₃ sec.-Butoxycarbonyl 557 CH₃ tert.-Butoxycarbonyl 558 CH₃ n-Hexoxycarbonyl 559 CH₃ Phenoxycarbonyl 560 CH₃ 4-Chlorophenoxycarbonyl 561 CH₃ Benzyloxycarbonyl 562 CH₃ Aminocarbonyl 563 CH₃ Dimethylaminocarbonyl 564 CH₃ Diethylaminocarbonyl 565 CH₃ Di-iso-Propylaminocarbonyl 566 CH₃ Phenylaminocarbonyl 567 CH₃ N-Methyl-N-Phenylaminocarbonyl 568 CH₃ Phenyl 569 CH₃ 2-Fluorophenyl oil; IR (film): 1708, 1634, 1257, 1129, 761 570 CH₃ 3-Fluorophenyl 571 CH₃ 4-Fluorophenyl m. p.: 67-68° C.; IR (KBr): 1691, 1629, 1295, 1253, 1132, 1037, 848 572 CH₃ Pentafluorophenyl 573 CH₃ 2-Chlorophenyl oil; — 574 CH₃ 3-Chlorophenyl 575 CH₃ 4-Chlorophenyl 576 CH₃ Pentachlorophenyl 577 CH₃ 2,3-Dichlorophenyl 578 CH₃ 2,4-Dichlorophenyl oil; IR (film): 1708, 1634, 1256, 1129 579 CH₃ 2,5-Dichlorophenyl m. p.: 80-2° C.; IR (KBr): 1704, 1634, 1250, 1132, 934, 766 580 CH₃ 2,6-Dichlorophenyl 581 CH₃ 3,4-Dichlorophenyl 582 CH₃ 3,5-Dichlorophenyl m. p.: 87-88° C.; IR (KBr): 1699, 1303, 1071, 1015, 932, 835 583 CH₃ 2,3,4-Trichlorophenyl oil; IR (film): 1709, 1627, 1257, 1131, 1109 584 CH₃ 2,3,5-Trichlorophenyl 585 CH₃ 2,3,6-Trichlorophenyl 586 CH₃ 2,4,5-Trichlorophenyl 587 CH₃ 2,4,6-Trichlorophenyl 588 CH₃ 3,4,5-Trichlorophenyl 589 CH₃ 2,3,4,6-Tetrachlorophenyl 590 CH₃ 2,3,5,6-Tetrachlorophenyl 591 CH₃ 2-Bromophenyl 592 CH₃ 3-Bromophenyl m. p.: 60-2° C.; IR (KBr): 1708, 1635, 1253, 1129, 1113, 933, 773 593 CH₃ 4-Bromophenyl m. p.: 104-6° C.; IR (KBr): 1694, 1620, 1296, 1264, 1035, 938 594 CH₃ 2,4-Dibromophenyl 595 CH₃ 3-Bromo-4-Fluorophenyl 596 CH₃ 3-Bromo-4-Methoxyphenyl 597 CH₃ 2-Iodophenyl 598 CH₃ 3-Iodophenyl 599 CH₃ 4-Iodophenyl 600 CH₃ 2-Chloro-4-fluorophenyl 601 CH₃ 2-Chloro-5-fluorophenyl 602 CH₃ 2-Chloro-6-fluorophenyl 603 CH₃ 2-Chloro-4-bromophenyl 604 CH₃ 2-Bromo-4-chlorophenyl 605 CH₃ 2-Bromo-4-fluorophenyl 606 CH₃ 3-Bromo-4-chlorophenyl 607 CH₃ 3-Chloro-4-fluorophenyl 608 CH₃ 3-Fluoro-4-chlorophenyl 609 CH₃ 2-Cyanophenyl 610 CH₃ 3-Cyanophenyl 611 CH₃ 4-Cyanophenyl 612 CH₃ 2-Nitrophenyl 613 CH₃ 3-Nitrophenyl 614 CH₃ 4-Nitrophenyl 615 CH₃ 2-Methylphenyl 616 CH₃ 3-Methylphenyl oil; IR (film): 1709, 1634, 1256, 1129 617 CH₃ 4-Methylphenyl m. p.: 73-75° C.; IR (KBr): 1696, 1625, 1262, 1127, 1037, 930 618 CH₃ 2,4-Dimethylphenyl 619 CH₃ 2,6-Dimethylphenyl 620 CH₃ 3,4-Dimethylphenyl 621 CH₃ 3,5-Dimethylphenyl 622 CH₃ 2,3,4-Trimethylphenyl 623 CH₃ 2,3,5-Trimethylphenyl 624 CH₃ 2,3,6-Trimethylphenyl 625 CH₃ 2,4,5-Trimethylphenyl 626 CH₃ 2,4,6-Trimethylphenyl 627 CH₃ 3,4,5-Trimethylphenyl 628 CH₃ Pentamethylphenyl 629 CH₃ 2-Ethylphenyl 630 CH₃ 3-Ethylphenyl 631 CH₃ 4-Ethylphenyl 632 CH₃ 3,5-Diethylphenyl 633 CH₃ 2-n-Propylphenyl 634 CH₃ 3-n-Propylphenyl 635 CH₃ 4-n-Propylphenyl 636 CH₃ 2-iso-Propylphenyl 637 CH₃ 3-iso-Propylphenyl 638 CH₃ 4-iso-Propylphenyl 639 CH₃ 2,4-Di-iso-Propylphenyl 640 CH₃ 3,5-Di-iso-Propylphenyl 641 CH₃ 4-n-Butylphenyl 642 CH₃ 4-sec.-Butylphenyl 643 CH₃ 4-iso-Butylphenyl 644 CH₃ 4-tert.-Butylphenyl 645 CH₃ 3-tert.-Butylphenyl 646 CH₃ 2-tert.-Butylphenyl 647 CH₃ 2,4-Di-tert.-Butylphenyl 648 CH₃ 3,5-Di-tert.-Butylphenyl 649 CH₃ 4-n-Hexylphenyl 650 CH₃ 4-n-Dodecylphenyl 651 CH₃ 2-Methyl-4-tert.-Butylphenyl 652 CH₃ 2-Methyl-6-tert.-Butylphenyl 653 CH₃ 2-Methyl-4-iso-Propylphenyl 654 CH₃ 2-Methyl-4-Cyclohexylphenyl 655 CH₃ 2-Methyl-4-Phenylphenyl 656 CH₃ 2-Methyl-4-Benzylphenyl 657 CH₃ 2-Methyl-4-Phenoxyphenyl 658 CH₃ 2-Methyl-4-Benzyloxyphenyl 659 CH₃ 2-Methyl-3-Chlorophenyl 660 CH₃ 2-Methyl-4-Chlorophenyl 661 CH₃ 2-Methyl-5-Chlorophenyl 662 CH₃ 2-Methyl-6-Chlorophenyl 663 CH₃ 2-Methyl-4-Fluorophenyl 664 CH₃ 2-Methyl-3-Bromophenyl 665 CH₃ 2-Methyl-4-Bromophenyl 666 CH₃ 2-Methyl-3-Methoxyphenyl 667 CH₃ 2-Methyl-4-Methoxyphenyl 668 CH₃ 2-Methyl-5-Methoxyphenyl 669 CH₃ 2-Methyl-6-Methoxyphenyl 670 CH₃ 2-Methyl-4-iso-Propoxyphenyl 671 CH₃ 2-Methyl-2,5-Dimethoxyphenyl 672 CH₃ 2-Methoxyphenyl 673 CH₃ 3-Methoxyphenyl oil; IR (film): 1708, 1634, 1285, 1256, 1129, 1111 674 CH₃ 4-Methoxyphenyl oil; IR (film): 1708, 1235, 1129 675 CH₃ 2,3-Dimethoxyphenyl 676 CH₃ 2,4-Dimethoxyphenyl 677 CH₃ 2,5-Dimethoxyphenyl 678 CH₃ 2,6-Dimethoxyphenyl 679 CH₃ 3,4-Dimethoxyphenyl 680 CH₃ 3,5-Dimethoxyphenyl 681 CH₃ 3,6-Dimethoxyphenyl 682 CH₃ 2,3,4-Trimethoxyphenyl 683 CH₃ 2,3,5-Trimethoxyphenyl 684 CH₃ 2,3,6-Trimethoxyphenyl 685 CH₃ 2,4,5-Trimethoxyphenyl 686 CH₃ 2,4,6-Trimethoxyphenyl 687 CH₃ 3,4,5-Trimethoxyphenyl 688 CH₃ 2-Ethoxyphenyl 689 CH₃ 3-Ethoxyphenyl 690 CH₃ 4-Ethoxyphenyl 691 CH₃ 2-iso-Propoxyphenyl 692 CH₃ 3-iso-Propoxyphenyl 693 CH₃ 4-iso-Propoxyphenyl 694 CH₃ 3-tert.-Butoxyphenyl 695 CH₃ 4-tert.-Butoxyphenyl 696 CH₃ 2-Trifluoromethoxyphenyl 697 CH₃ 3-Trifluoromethoxyphenyl 698 CH₃ 4-Trifluoromethoxyphenyl 699 CH₃ 3-(1′,1′,2′,2′-Tetrafluoro)ethoxyphenyl 700 CH₃ 4-(1′,1′,2′,2′-Tetrafluoro)ethoxyphenyl 701 CH₃ 2-Chloromethylphenyl 702 CH₃ 3-Chloromethylphenyl 703 CH₃ 4-Chloromethylphenyl 704 CH₃ 2-Trifluoromethylphenyl oil; IR (film): 1705, 1634, 1313, 1130, 1107, 767 705 CH₃ 3-Trifluoromethylphenyl oil; IR (film): 1710, 1635, 1276, 1128 706 CH₃ 4-Trifluoromethylphenyl m. p.: 104-5° C.; IR (KBr): 1697, 1628, 1323, 1123 707 CH₃ 2-(Methoxyiminomethyl)phenyl 708 CH₃ 3-(Methoxyiminomethyl)phenyl 709 CH₃ 4-(Methoxyiminomethyl)phenyl 710 CH₃ 2-(Ethoxyiminomethyl)phenyl 711 CH₃ 3-(Ethoxyiminomethyl)phenyl 712 CH₃ 4-(Ethoxyiminomethyl)phenyl 713 CH₃ 2-(n-Propoxyiminomethyl)phenyl 714 CH₃ 3-(n-Propoxyiminomethyl)phenyl 715 CH₃ 4-(n-Propoxyiminomethyl)phenyl 716 CH₃ 2-(iso-Propoxyiminomethyl)phenyl 717 CH₃ 3-(iso-Propoxyiminomethyl)phenyl 718 CH₃ 4-(iso-Propoxyiminomethyl)phenyl 719 CH₃ 2-(n-Butoxyiminomethyl)phenyl 720 CH₃ 3-(n-Butoxyiminomethyl)phenyl 721 CH₃ 4-(n-Butoxyiminomethyl)phenyl 722 CH₃ 2-(iso-Butoxyiminomethyl)phenyl 723 CH₃ 3-(iso-Butoxyiminomethyl)phenyl 724 CH₃ 4-(iso-Butoxyiminomethyl)phenyl 725 CH₃ 2-(tert.-Butoxyiminomethyl)phenyl 726 CH₃ 3-(tert.-Butoxyiminomethyl)phenyl 727 CH₃ 4-(tert.-Butoxyiminomethyl)phenyl 728 CH₃ 2-(n-Pentoxyiminomethyl)phenyl 729 CH₃ 3-(n-Pentoxyiminomethyl)phenyl 730 CH₃ 4-(n-Pentoxyiminomethyl)phenyl 731 CH₃ 2-(n-Hexoxyiminomethyl)phenyl 732 CH₃ 3-(n-Hexoxyiminomethyl)phenyl 733 CH₃ 4-(n-Hexoxyiminomethyl)phenyl 734 CH₃ 2-(Allyloxyiminomethyl)phenyl 735 CH₃ 3-(Allyloxyiminomethyl)phenyl 736 CH₃ 4-(Allyloxyiminomethyl)phenyl 737 CH₃ 2-(Benzyloxyiminomethyl)phenyl 738 CH₃ 3-(Benzyloxyiminomethyl)phenyl 739 CH₃ 4-(Benzyloxyiminomethyl)phenyl 740 CH₃ 2-(Methoxyimino-1′-ethyl)phenyl 741 CH₃ 3-(Methoxyimino-1′-ethyl)phenyl 742 CH₃ 4-(Methoxyimino-1′-ethyl)phenyl 743 CH₃ 2-(Ethoxyimino-1′-ethyl)phenyl 744 CH₃ 3-(Ethoxyimino-1′-ethyl)phenyl 745 CH₃ 4-(Ethoxyimino-1′-ethyl)phenyl 746 CH₃ 2-(n-Propoxyimino-1′-ethyl)phenyl 747 CH₃ 3-(n-Propoxyimino-1′-ethyl)phenyl 748 CH₃ 4-(n-Propoxyimino-1′-ethyl)phenyl 749 CH₃ 2-(n-Butoxyimino-1′-ethyl)phenyl 750 CH₃ 3-(n-Butoxyimino-1′-ethyl)phenyl 751 CH₃ 4-(n-Butoxyimino-1′-ethyl)phenyl 752 CH₃ 2-(n-Pentoxyimino-1′-ethyl)phenyl 753 CH₃ 3-(n-Pentoxyimino-1′-ethyl)phenyl 754 CH₃ 4-(n-Pentoxyimino-1′-ethyl)phenyl 755 CH₃ 2-(n-Hexoxyimino-1′-ethyl)phenyl 756 CH₃ 3-(n-Hexoxyimino-1′-ethyl)phenyl 757 CH₃ 4-(n-Hexoxyimino-1′-ethyl)phenyl 758 CH₃ 2-(Allyloxyimino-1′-ethyl)phenyl 759 CH₃ 3-(Allyloxyimino-1′-ethyl)phenyl 760 CH₃ 4-(Allyloxyimino-1′-ethyl)phenyl 761 CH₃ 2-(Benzyloxyimino-1′-ethyl)phenyl 762 CH₃ 3-(Benzyloxyimino-1′-ethyl)phenyl 763 CH₃ 4-(Benzyloxyimino-1′-ethyl)phenyl 764 CH₃ 2-Phenylphenyl 765 CH₃ 3-Phenylphenyl 766 CH₃ 4-Phenylphenyl 767 CH₃ 2-Phenoxyphenyl 768 CH₃ 3-Phenoxyphenyl 769 CH₃ 4-Phenoxyphenyl oil; IR (film): 1708, 1489, 1240, 1129 770 CH₃ 2-Benzyloxyphenyl 771 CH₃ 3-Benzyloxyphenyl 772 CH₃ 4-Benzyloxyphenyl 773 CH₃ 4-(Imidazol-1′-yl)phenyl 774 CH₃ 4-(Piperazin-1′-yl)phenyl 775 CH₃ 4-(Morpholin-1′-yl)phenyl 776 CH₃ 4-(Piperidin-1′-yl)phenyl 777 CH₃ 4-(Pyridyl-1′-yl)phenyl 778 CH₃ 2-Cyclopropylphenyl 779 CH₃ 3-Cyclopropylphenyl 780 CH₃ 4-Cyclopropylphenyl 781 CH₃ 3-Cyclohexylphenyl 782 CH₃ 4-Cyclohexylphenyl 783 CH₃ 4-Oxiranylphenyl 784 CH₃ 4-(1′,3′-Dioxan-2′-yl)phenyl 785 CH₃ 4-(Tetrahydropyran-2-yloxy)phenyl 786 CH₃ 1-Naphthyl 787 CH₃ 2-Naphthyl 788 CH₃ 9-Anthryl 789 CH₃ 1-Naphthoxy 790 CH₃ 2-Naphthoxy 791 CH₃ 9-Anthroxy 792 CH₃ Phenoxy 793 CH₃ 2-Chlorophenoxy 794 CH₃ 3-Chlorophenoxy 795 CH₃ 4-Chlorophenoxy 796 CH₃ 4-Methylphenoxy 797 CH₃ 4-tert.-Butylphenoxy 798 CH₃ 4-Methoxyphenoxy 799 CH₃ 4-Ethoxyphenoxy 800 CH₃ 4-tert.-Butoxyphenoxy 801 CH₃ Phenylthio 802 CH₃ 2-Chlorophenylthio 803 CH₃ 4-Chlorophenylthio 804 CH₃ Benzyl 805 CH₃ 2-Methylbenzyl 806 CH₃ 3-Methylbenzyl 807 CH₃ 4-Methylbenzyl 808 CH₃ 4-tert.-Butylbenzyl 809 CH₃ 2-Chlorobenzyl 810 CH₃ 3-Chlorobenzyl 811 CH₃ 4-Chlorobenzyl 812 CH₃ 2,4-Dichlorobenzyl 813 CH₃ 2,6-Dichlorobenzyl 814 CH₃ 2,4,6-Trichlorobenzyl 815 CH₃ 2-Trifluoromethylbenzyl 816 CH₃ 3-Trifluoromethylbenzyl 817 CH₃ 4-Trifluoromethylbenzyl 818 CH₃ 2-Methoxybenzyl 819 CH₃ 4-Methoxybenzyl 820 CH₃ 4-tert.-Butoxybenzyl 821 CH₃ 4-Phenoxybenzyl 822 CH₃ 1-Phenethyl 823 CH₃ 2-Phenethyl 824 CH₃ 1-Phenylpropyl 825 CH₃ 2-Phenylpropyl 826 CH₃ 3-Phenylpropyl 827 CH₃ 2-Methyl-2-phenylpropyl 828 CH₃ 2-Methyl-3-phenylpropyl 829 CH₃ 4-Phenylbutyl 830 CH₃ 2-Phenyl-1-ethenyl 831 CH₃ 1-Phenyl-1-ethenyl 832 CH₃ 1-Phenyl-1-propenyl 833 CH₃ 1-Phenyl-1-propen-2-yl 834 CH₃ 2,3-Diphenylethenyl 835 CH₃ Phenoxymethyl 836 CH₃ 2-Pyridyl 837 CH₃ 3-Pyridyl 838 CH₃ 4-Pyridyl 839 CH₃ 2,6-Pyrimidienyl 840 CH₃ 1,5-Pyrimidienyl 841 CH₃ 2-Thienyl 842 CH₃ 3-Thienyl 843 CH₃ 2-Furyl 844 CH₃ 3-Furyl 845 CH₃ 1-Pyrrolyl 846 CH₃ 1-Imidazolyl 847 CH₃ 1,2,4-Triazolyl 848 CH₃ 1,3,4-Triazolyl 849 CH₃ 4-Thiazolyl 850 CH₃ 3-Benzothiazolyl 851 CH₃ 2-Pyridyloxy 852 CH₃ 2-Pyrimidinyloxy 853 CH₃ 2-Pyridylthio 854 CH₃ 2-Pyrimidinylthio 855 CH₃ 2-Benzothiazolylthio 856 CH₃ Phenylthiomethyl 857 CH₃ 2-Pyridylmethyl 858 CH₃ 3-Pyridylmethyl 859 CH₃ Furfuryloxy 860 CH₃ Thienylmethoxy 861 CH₃ 3-Isoazolylmethoxy 862 CH₃ 2-Oxazolylmethoxy 863 CH₃ 2-Pyridylmethoxy 864 CH₃ 2′-Furyl-2-ethenyl 865 CH₃ 2′-Thienyl-2-ethenyl 866 CH₃ 3′-Pyridyl-2-ethenyl 867 CH₃ Oziranyl 868 CH₃ 1-Aziridinyl 869 CH₃ 1-Azetidinyl 870 CH₃ 1-Pyrrolidinyl 871 CH₃ 2-Tetrahydrofuryl 872 CH₃ 2-Tetrahydropyranyl 873 CH₃ 3-Tetrahydropyranyl 874 CH₃ 1-Piperidinyl 875 CH₃ 1-Morpholinyl 876 CH₃ 1-Piperazinyl 877 CH₃ 1,3-Dioxan-2-yl 878 CH₃ 3-Tetrahydrothiopyranyl 879 CH₃ 2-Dihydropyranyloxy 880 CH₃ 2-Tetrahydropyranyloxy 881 CH₃ CF₃ 882 CH₃ 2-Fluoroethyl 883 CH₃ 2,2,2-Trifluoroethyl 884 CH₃ Pentafluoroethyl 885 CH₃ Chloromethyl 886 CH₃ Dichloromethyl 887 CH₃ Trichloromethyl 888 CH₃ 2-Chloroethyl 889 CH₃ 2,2,2-Trichloroethyl 890 CH₃ Pentachloroethyl 891 CH₃ Cyclopropyl 892 CH₃ Cyclobutyl 893 CH₃ Cyclopentyl 894 CH₃ Cyclohexyl 895 CH₃ 1-Methylcyclopropyl 896 CH₃ 2,2-Dimethylcyclopropyl 897 CH₃ 1-Methylcyclohexyl 898 CH₃ 2,2-Difluorocyclopropyl 899 CH₃ 2,2-Dichlorocyclopropyl 900 CH₃ 2,2-Dibromocyclopropyl 901 CH₃ 2,2-Dichloro-3-methylcyclopropyl 902 CH₃ 2,2,3,3-Tetrafluorocyclobutyl 903 CH₃ Ethenyl 904 CH₃ 1-Propenyl 905 CH₃ 2-Methyl-1-propenyl 906 CH₃ 4-Methylpent-3-en-1-yl 907 CH₃ 2-Propenyl 908 CH₃ 2-Butenyl 909 CH₃ 1-Methyl-2-propenyl 910 CH₃ 3-Methyl-2-butenyl 911 CH₃ 2,2-Difluoroethenyl 912 CH₃ 2,2-Dichloroethenyl 913 CH₃ 3,3,3-Trifluoropropenyl 914 CH₃ 3,3,3-Trichloropropenyl 915 CH₃ 3-Chloro-2-propenyl 916 CH₃ Cyclopent-1-enyl 917 CH₃ Cyclopentadienyl 918 CH₃ Cyclohex-1-enyl 919 CH₃ Pentafluorocyclopentadienyl 920 CH₃ Pentachlorocyclopentadienyl 921 Phenyl Phenyl 922 Phenyl 2-Fluorophenyl 923 Phenyl 4-Fluorophenyl 924 Phenyl 2-Chlorophenyl 925 Phenyl 3-Chlorophenyl 926 Phenyl 4-Chlorophenyl 927 Phenyl 3,4-Dichlorophenyl 928 Phenyl 4-Nitrophenyl 929 Phenyl 2-CF₃-Phenyl 930 Phenyl 3-CF₃-Phenyl 931 Phenyl 4-CF₃-Phenyl 932 Phenyl 2-Methylphenyl 933 Phenyl 3-Methylphenyl 934 Phenyl 4-Methylphenyl 935 Phenyl 2,4-Dimethylphenyl 936 Phenyl 4-tert.-Butylphenyl 937 Phenyl 4-Methoxyphenyl 938 4-Fluorophenyl 4-Fluorophenyl 939 2-Fluorophenyl 4-Fluorophenyl 940 2-Chlorophenyl 4-Fluorophenyl 941 2-Chlorophenyl 2-Chlorophenyl 942 3-Chlorophenyl 3-Chlorophenyl 943 4-Chlorophenyl 4-Chlorophenyl 944 2-Chlorophenyl 4-Chlorophenyl 945 4-Methoxyphenyl 4-Methoxyphenyl 946 4-Dimethylaminophenyl 4-Dimethylaminophenyl 947 Phenyl Naphthyl 948 Ethyl Ethyl 949 Ethyl n-Propyl 950 Ethyl iso-Propyl 951 Ethyl n-Butyl 952 Ethyl iso-Butyl 953 Ethyl 2-Methyl-butyl 954 Ethyl Benzyl 955 n-Propyl n-Propyl 956 iso-Propyl iso-Propyl 957 n-Butyl n-Butyl 958 iso-Butyl iso-Butyl 959 tert.-Butyl tert.-Butyl 960 Benzyl Benzyl 961 Pentachloroethyl Pentachloroethyl 962 n-Hexyl n-Hexyl 963 Ethoxycarbonyl Ethoxycarbonyl 964 Phenyl Benzoyl 965 Ethyl Phenyl 966 n-Butyl Phenyl 967 Styryl Styryl 968 2-Pyridyl 2-Pyridyl 969 3-Pyridyl 3-Pyridyl 970 CH₃ 3,5-Dibenzyloxyphenyl IR (film): 1707, 1581, 1256, 1157, 1129

TABLE II

No. R³ R⁴ Data 1 Cl Phenyl 2 Cl Cyano 3 Cl Ethoxycarbonyl 4 Cl Cyclopropyl 5 CF₃ CF₃ 6 CF₃ Phenyl 7 CCl₃ CCl₃ 8 CCl₃ Phenyl 9 CH₂Cl Phenyl 10 CF₂CF₃ Phenyl 11 CF₂Cl Phenyl 12 CHCl₂ Phenyl 13 Cyclopropyl Cyclopropyl 14 Cyclopropyl Phenyl oil; IR (film): 1437, 1321, 1219, 1045, 983, 766 15 Cyclopropyl 4-Fluorophenyl oil; IR (film): 1508, 1321, 1222, 1046, 985, 839 16 Cyclopropyl 4-Chlorophenyl oil; IR (film): 1489, 1321, 1218, 1090, 1046, 829 17 Cyclopropyl 4-Methoxyphenyl oil; IR (film): 1300, 1250, 1218, 983, 833 18 Cyclopropyl 4-Ethoxyphenyl 19 Cyclopropyl 4-Phenoxyphenyl 20 Cyclopropyl Pentachlorophenyl 21 Cyclopropyl Pentafluorophenyl 22 Cyclopentyl Phenyl 23 Cyclohexyl Phenyl 24 Phenyl 2,2-Dichloro-1-methylcyclopropyl 25 Phenyl 2,2-Difluorocyclopropyl 26 Phenyl 2,2-Dichlorocyclopropyl 27 Phenyl 2,2-Dibromocyclopropyl 28 Phenyl 2,2,3,3-Tetrafluorocyclobutyl 29 Phenyl 2,2-Dimethylcyclopropyl 30 Phenyl 1-Methylcyclohexyl 31 CN Methoxymethyl 32 CN Ethoxymethyl 33 CN n-Propoxymethyl 34 CN iso-Propoxymethyl 35 CN tert.-Butoxymethyl 36 CN 2-Methoxyprop-2-yl m.p.: 83° C.; IR (KBr): 1437, 1223, 1206, 1069, 1006 37 CN 2-Ethoxyprop-2-yl oil; IR (film): 1439, 3122, 1221, 1202, 1048 38 CN 2-n-Propoxyprop-2-yl oil; IR (film): 1438, 1322, 1221, 1203, 1048 39 CN 2-iso-Propoxyprop-2-yl m.p.: 74-5° C.; IR (KBr): 1302, 1231, 1169, 1108, 1079, 997, 757 40 CN 2-tert.-Butoxyprop-2-yl 41 CN Methylthiomethyl 42 CN tert.-Butylthiomethyl 43 CN 2-Methylthioprop-2-yl m.p.: 107° C.; IR (KBr): 1434, 1297, 1126, 1066, 1010, 769 44 CN 2-iso-Propylthioprop-2-yl oil; IR (film): 1438, 1366, 1321, 1221, 1202 45 CN 2-tert.-Butylthioprop-2-yl 46 CN Methyl 47 CN Ethyl 48 CN n-Propyl 49 CN iso-Propyl oil; IR (film): 1439, 1321, 1222, 1012, 767 50 CN n-Butyl 51 CN iso-Butyl 52 CN sec.-Butyl 53 CN tert.-Butyl 54 CN n-Hexyl 55 CN n-Decyl 56 CN Cyclopropyl m.p.: 74-75° C.; IR (KBr): 1433, 1223, 1043, 763 57 CN Cyclohexyl 58 CN Phenylthiomethyl 59 CN 2-Phenylthiomethyl 60 CN 2-(2′-Chlorophenylthio)prop-2-yl 61 CN Ethynyl 62 CN 1-Propynyl 63 CN Methoxy 64 CN Ethoxy 65 CN n-Propoxy 66 CN iso-Propoxy 67 CN n-Butoxy 68 CN iso-Butoxy 69 CN sec.-Butoxy 70 CN tert.-Butoxy 71 CN Methylthio 72 CN Ethylthio 73 CN n-Propylthio 74 CN iso-Propylthio 75 CN n-Butylthio 76 CN iso-Butylthio 77 CN sec.-Butylthio 78 CN tert.-Butylthio 79 CN Benzylthio 80 CN Trifluoromethoxy 81 CN Cyano 82 CN Amino 83 CN Methylamino 84 CN Dimethylamino 85 CN Ethylamino 86 CN Diethylamino 87 CN Di-n-Propylamino 88 CN Di-iso-Propylamino 89 CN Di-n-Butylamino 90 CN Di-iso-Butylamino 91 CN Acetyl 92 CN Propion-1-yl 93 CN Butyr-1-yl 94 CN iso-Butyr-1-yl 95 CN Pivaloyl 96 CN Benzoyl 97 CN 4-Chlorobenzoyl 98 CN Benzylcarbonyl 99 CN Methoxycarbonyl 100 CN Ethoxycarbonyl 101 CN n-Propoxycarbonyl 102 CN iso-Propoxycarbonyl 103 CN n-Butoxycarbonyl 104 CN iso-Butoxycarbonyl 105 CN sec.-Butoxycarbonyl 106 CN tert.-Butoxycarbonyl 107 CN n-Hexoxycarbonyl 108 CN Phenoxycarbonyl 109 CN 4-Chlorophenoxycarbonyl 110 CN Benzyloxycarbonyl 111 CN Aminocarbonyl 112 CN Dimethylaminocarbonyl 113 CN Diethylaminocarbonyl 114 CN Di-iso-Propylaminocarbonyl 115 CN Phenylaminocarbonyl 116 CN N-Methyl-N-Phenylaminocarbonyl 117 CN Phenyl m.p.: 99-100° C.; IR (KBr): 1436, 1215, 1208, 1097, 1026, 944, 766, 690 118 CN 2-Fluorophenyl 119 CN 3-Fluorophenyl 120 CN 4-Fluorophenyl 121 CN Pentafluorophenyl 122 CN 2-Chlorophenyl 123 CN 3-Chlorophenyl 124 CN 4-Chlorophenyl 125 CN Pentachlorophenyl 126 CN 2,3-Dichlorophenyl 127 CN 2,4-Dichlorophenyl 128 CN 2,5-Dichlorophenyl 129 CN 2,6-Dichlorophenyl 130 CN 3,4-Dichlorophenyl 131 CN 3,5-Dichlorophenyl 132 CN 2,3,4-Trichlorophenyl 133 CN 2,3,5-Trichlorophenyl 134 CN 2,3,6-Trichlorophenyl 135 CN 2,4,5-Trichlorophenyl 136 CN 2,4,6-Trichlorophenyl 137 CN 3,4,5-Trichlorophenyl 138 CN 2,3,4,6-Tetrachlorophenyl 139 CN 2,3,5,6-Tetrachlorophenyl 140 CN 2-Bromophenyl 141 CN 3-Bromophenyl 142 CN 4-Bromophenyl 143 CN 2,4-Dibromophenyl 144 CN 3-Bromo-4-fluorophenyl 145 CN 3-Bromo-4-methoxyphenyl 146 CN 2-Iodophenyl 147 CN 3-Iodophenyl 148 CN 4-Iodophenyl 149 CN 2-Chloro-4-fluorophenyl 150 CN 2-Chloro-5-fluorophenyl 151 CN 2-Chloro-6-fluorophenyl 152 CN 2-Chloro-4-bromophenyl 153 CN 2-Bromo-4-chlorophenyl 154 CN 2-Bromo-4-fluorophenyl 155 CN 3-Bromo-4-chlorophenyl 156 CN 3-Chloro-4-fluorophenyl 157 CN 3-Fluoro-4-chlorophenyl 158 CN 2-Cyanophenyl 159 CN 3-Cyanophenyl 160 CN 4-Cyanophenyl 161 CN 2-Nitrophenyl 162 CN 3-Nitrophenyl 163 CN 4-Nitrophenyl 164 CN 2-Methylphenyl 165 CN 3-Methylphenyl 166 CN 4-Methylphenyl 167 CN 2,4-Dimethylphenyl 168 CN 2,6-Dimethylphenyl 169 CN 3,4-Dimethylphenyl 170 CN 3,5-Dimethylphenyl 171 CN 2,3,4-Trimethylphenyl 172 CN 2,3,5-Trimethylphenyl 173 CN 2,3,6-Trimethylphenyl 174 CN 2,4,5-Trimethylphenyl 175 CN 2,4,6-Trimethylphenyl 176 CN 3,4,5-Trimethylphenyl 177 CN Pentamethylphenyl 178 CN 2-Ethylphenyl 179 CN 3-Ethylphenyl 180 CN 4-Ethylphenyl 181 CN 3,5-Diethylphenyl 182 CN 2-n-Propylphenyl 183 CN 3-n-Propylphenyl 184 CN 4-n-Propylphenyl 185 CN 2-iso-Propylphenyl 186 CN 3-iso-Propylphenyl 187 CN 4-iso-Propylphenyl 188 CN 2,4-Di-iso-Propylphenyl 189 CN 3,5-Di-iso-Propylphenyl 190 CN 4-n-Butylphenyl 191 CN 4-sec.-Butylphenyl 192 CN 4-iso-Butylphenyl 193 CN 4-tert.-Butylphenyl 194 CN 3-tert.-Butylphenyl 195 CN 2-tert.-Butylphenyl 196 CN 2,4-Di-tert.-Butylphenyl 197 CN 3,5-Di-tert.-Butylphenyl 198 CN 4-n-Hexylphenyl 199 CN 4-n-Dodecylphenyl 200 CN 2-Methyl-4-tert.-Butylphenyl 201 CN 2-Methyl-6-tert.-Butylphenyl 202 CN 2-Methyl-4-iso-Propylphenyl 203 CN 2-Methyl-4-Cyclohexylphenyl 204 CN 2-Methyl-4-Phenylphenyl 205 CN 2-Methyl-4-Benxylphenyl 206 CN 2-Methyl-4-Phenoxyphenyl 207 CN 2-Methyl-4-Benxyloxyphenyl 208 CN 2-Methyl-3-Chlorophenyl 209 CN 2-Methyl-4-Chlorophenyl 210 CN 2-Methyl-5-Chlorophenyl 211 CN 2-Methyl-6-Chlorophenyl 212 CN 2-Methyl-4-Fluorophenyl 213 CN 2-Methyl-3-Bromophenyl 214 CN 2-Methyl-4-Bromophenyl 215 CN 2-Methyl-3-Methoxyphenyl 216 CN 2-Methyl-4-Methoxyphenyl 217 CN 2-Methyl-5-Methoxyphenyl 218 CN 2-Methyl-6-Methoxyphenyl 219 CN 2-Methyl-4-iso-Propoxyphenyl 220 CN 2-Methyl-2-,5-Dimethoxyphenyl 221 CN 2-Methoxyphenyl 222 CN 3-Methoxyphenyl 223 CN 4-Methoxyphenyl 224 CN 2,3-Dimethoxyphenyl 225 CN 2,4-Dimethoxyphenyl 226 CN 2,5-Dimethoxyphenyl 227 CN 2,6-Dimethoxyphenyl 228 CN 3,4-Dimethoxyphenyl 229 CN 3,5-Dimethoxyphenyl 230 CN 3,6-Dimethoxyphenyl 231 CN 2,3,4-Trimethoxyphenyl 232 CN 2,3,5-Trimethoxyphenyl 233 CN 2,3,6-Trimethoxyphenyl 234 CN 2,4,5-Trimethoxyphenyl 235 CN 2,4,6-Trimethoxyphenyl 236 CN 3,4,5-Trimethoxyphenyl 237 CN 2-Ethoxyphenyl 238 CN 3-Ethoxyphenyl 239 CN 4-Ethoxyphenyl 240 CN 2-iso-Propoxyphenyl 241 CN 3-iso-Propoxyphenyl 242 CN 4-iso-Propoxyphenyl 243 CN 3-tert.-Butoxyphenyl 244 CN 4-tert.-Butoxyphenyl 245 CN 2-Trifluoromethoxyphenyl 246 CN 3-Trifluoromethoxyphenyl 247 CN 4-Trifluoromethoxyphenyl 248 CN 3-(1′,1′,2′,2′-Tetrafluoro)ethoxyphenyl 249 CN 4-(1′,1′,2′,2′-Tetrafluoro)ethoxyphenyl 250 CN 2-Chloromethylphenyl 251 CN 3-Chloromethylphenyl 252 CN 4-Chloromethylphenyl 253 CN 2-Trifluoromethylphenyl 254 CN 3-Trifluoromethylphenyl 255 CN 4-Trifluoromethylphenyl 256 CN 2-(Methoxyiminomethyl)phenyl 257 CN 3-(Methoxyiminomethyl)phenyl 258 CN 4-(Methoxyiminomethyl)phenyl 259 CN 2-(Ethoxyiminomethyl)phenyl 260 CN 3-(Ethoxyiminomethyl)phenyl 261 CN 4-(Ethoxyiminomethyl)phenyl 262 CN 2-(n-Propoxyiminomethyl)phenyl 263 CN 3-(n-Propoxyiminomethyl)phenyl 264 CN 4-(n-Propoxyiminomethyl)phenyl 265 CN 2-(iso-Propoxyiminomethyl)phenyl 266 CN 3-(iso-Propoxyiminomethyl)phenyl 267 CN 4-(iso-Propoxyiminomethyl)phenyl 268 CN 2-(n-Butoxyiminomethyl)phenyl 269 CN 3-(n-Butoxyiminomethyl)phenyl 270 CN 4-(n-Butoxyiminomethyl)phenyl 271 CN 2-(iso-Butoxyiminomethyl)phenyl 272 CN 3-(iso-Butoxyiminomethyl)phenyl 273 CN 4-(iso-Butoxyiminomethyl)phenyl 274 CN 2-(tert.-Butoxyiminomethyl)phenyl 275 CN 3-(tert.-Butoxyiminomethyl)phenyl 276 CN 4-(tert.-Butoxyiminomethyl)phenyl 277 CN 2-(n-Pentoxyiminomethyl)phenyl 278 CN 3-(n-Pentoxyiminomethyl)phenyl 279 CN 4-(n-Pentoxyiminomethyl)phenyl 280 CN 2-(n-Hexoxyiminomethyl)phenyl 281 CN 3-(n-Hexoxyiminomethyl)phenyl 282 CN 4-(n-Hexoxyiminomethyl)phenyl 283 CN 2-(Allyloxyiminomethyl)phenyl 284 CN 3-(Allyloxyiminomethyl)phenyl 285 CN 4-(Allyloxyiminomethyl)phenyl 286 CN 2-(Benzyloxyiminomethyl)phenyl 287 CN 3-(Benzyloxyiminomethyl)phenyl 288 CN 4-(Benzyloxyiminomethyl)phenyl 289 CN 2-(Methoxyimino-1′-ethyl)phenyl 290 CN 3-(Methoxyimino-1′-ethyl)phenyl 219 CN 4-(Methoxyimino-1′-ethyl)phenyl 292 CN 2-(Ethoxyimino-1′-ethyl)phenyl 293 CN 3-(Ethoxyimino-1′-ethyl)phenyl 294 CN 4-(Ethoxyimino-1′-ethyl)phenyl 295 CN 2-(n-Propoxyimino-1′-ethyl)phenyl 296 CN 3-(n-Propoxyimino-1′-ethyl)phenyl 297 CN 4-(n-Propoxyimino-1′-ethyl)phenyl 298 CN 2-(n-Butoxyamino-1′-ethyl)phenyl 299 CN 3-(n-Butoxyamino-1′-ethyl)phenyl 300 CN 4-(n-Butoxyamino-1′-ethyl)phenyl 301 CN 2-(n-Pentoxyimino-1′-ethyl)phenyl 302 CN 3-(n-Pentoxyimino-1′-ethyl)phenyl 303 CN 4-(n-Pentoxyimino-1′-ethyl)phenyl 304 CN 2-(n-Hexoxyimino-1′-ethyl)phenyl 305 CN 3-(n-Hexoxyimino-1′-ethyl)phenyl 306 CN 4-(n-Hexoxyimino-1′-ethyl)phenyl 307 CN 2-(Allyloxyimino-1′-ethyl)phenyl 308 CN 3-(Allyloxyimino-1′-ethyl)phenyl 309 CN 4-(Allyloxyimino-1′-ethyl)phenyl 310 CN 2-(Benzyloxyimino-1′-ethyl)phenyl 311 CN 3-(Benzyloxyimino-1′-ethyl)phenyl 312 CN 4-(Benzyloxyimino-1′-ethyl)phenyl 313 CN 2-Phenylphenyl 314 CN 3-Phenylphenyl 315 CN 4-Phenylphenyl 316 CN 2-Phenoxyphenyl 317 CN 3-Phenoxyphenyl 318 CN 4-Phenoxyphenyl 319 CN 2-Benzyloxyphenyl 320 CN 3-Benzyloxyphenyl 321 CN 4-Benzyloxyphenyl 322 CN 4-(Imidazol-1′-yl)phenyl 323 CN 4-(Piperazin-1′-yl)phenyl 324 CN 4-(Morpholin-1′-yl)phenyl 325 CN 4-(Piperdin-1′-yl)phenyl 326 CN 4-(Pyridyl-2′-oxy)phenyl 327 CN 2-Cyclopropylphenyl 328 CN 3-Cyclopropylphenyl 329 CN 4-Cyclopropylphenyl 330 CN 3-Cyclohexylphenyl 331 CN 4-Cyclohexylphenyl 332 CN 4-Oxiranylphenyl 333 CN 4-(1′,3′-Dioxan-2′-yl)phenyl 334 CN 4-(Tetrahydropyran-2-yloxy)phenyl 335 CN 1-Naphthyl 336 CN 2-Naphthyl 337 CN 9-Anthryl 338 CN 1-Naphthoxy 339 CN 2-Naphthoxy 340 CN 9-Anthroxy 341 CN Phenoxy 342 CN 2-Chlorophenoxy 343 CN 3-Chlorophenoxy 344 CN 4-Chlorophenoxy 345 CN 4-Methylphenoxy 346 CN 4-tert.-Butylphenoxy 347 CN 4-Methoxyphenoxy 348 CN 4-Ethoxyphenoxy 349 CN 4-tert.-Butoxyphenoxy 350 CN Phenylthio 351 CN 2-Chlorophenylthio 352 CN 4-Chlorophenylthio 353 CN Benzyl 354 CN 2-Methylbenzyl 355 CN 3-Methylbenzyl 356 CN 4-Methylbenzyl 357 CN 4-tert.-Butylbenzyl 358 CN 2-Chlorobenzyl 359 CN 3-Chlorobenzyl 360 CN 4-Chlorobenzyl 361 CN 2,4-Dichlorobenzyl 362 CN 2,6-Dichlorobenzyl 363 CN 2,4,6-Trichlorobenzyl 364 CN 2-Trifluoromethylbenzyl 365 CN 3-Trifluoromethylbenzyl 366 CN 4-Trifluoromethylbenzyl 367 CN 2-Methoxybenzyl 368 CN 4-Methoxybenzyl 369 CN 4-tert.-Butoxybenzyl 370 CN 4-Phenoxybenzyl 371 CN 1-Phenethyl 372 CN 2-Phenethyl 373 CN 1-Phenylpropyl 374 CN 2-Phenylpropyl 375 CN 3-Phenylpropyl 376 CN 2-Methyl-2-phenylpropyl 377 CN 2-Methyl-3-phenylpropyl 378 CN 4-Phenylbutyl 379 CN 2-Phenyl-1-ethenyl 380 CN 1-Phenyl-1-ethenyl 381 CN 1-Phenyl-1-propenyl 382 CN 1-Phenyl-1-propen-2-yl 383 CN 2,2-Diphenylethenyl 384 CN Phenoxymethyl 385 CN 2-Pyridyl 386 CN 3-Pyridyl 387 CN 4-Pyridyl 388 CN 2,6-Pyrimidinyl 389 CN 1,5-Pyrimidinyl 390 CN 2-Thienyl 391 CN 3-Thienyl 392 CN 2-Furyl 393 CN 3-Furyl 394 CN 1-Pyrrolyl 395 CN 1-Imidazolyl 396 CN 1,2,4-Trimzolyl 397 CN 1,3,4-Triazolyl 398 CN 4-Thiazolyl 399 CN 2-Benzothiazolyl 400 CN 2-Pyridyloxy 401 CN 2-Pyrimidimyloxy 402 CN 2-Pyridylthio 403 CN 2-Pyrimidimylthio 404 CN 2-Benzothiazolythio 405 CN Phenylthiomethyl 406 CN 2-Pyridylmethyl 407 CN 3-Pyridylmethyl 408 CN Ferfuryloxy 409 CN Thienylmethoxy 410 CN 3-Isozazolylmethoxy 411 CN 2-Oxazolylmethoxy 412 CN 2-Pyridylmethoxy 413 CN 2′-Furyl-2-ethenyl 414 CN 2′-Thienyl-2-ethenyl 415 CN 3′-Pyridyl-2-ethenyl 416 CN Oxionyl 417 CN 1-Aziridinyl 418 CN 1-Azoxidinyl 419 CN 1-Pyrrolidinyl 420 CN 2-Tetrahydrofuryl 421 CN 2-Tetrahydropyranyl 422 CN 3-Tetrahydropyranyl 423 CN 1-Piperidinyl 424 CN 1-Morphotinyl 425 CN 1-Piperazinyl 426 CN 1,3-Dioxan-2-yl 427 CN 3-Tetrahydrothiopyranyl 428 CN 2-Dihydropyranyloxy 429 CN 2-Tetrahydrophyranyloxy oil; IR (film): 1439, 1228, 1209, 1050, 1025, 767 430 CN (CH₂)₄ 431 CN (CH₂)₅ 432 CN (CH₂)₆ 433 CN 434 CN 435 CN

436 CN

437 CN

438 CN

439 CN

440 CN

441 CN CF₃ 442 CN 2-Fluoroethyl 443 CN 2,2,2-Trifluoroethyl 444 CN Pentafluoroethyl 445 CN Chloromethyl 446 CN Dichloromethyl 447 CN Trichloromethyl 448 CN 2-Chloroethyl 449 CN 2,2,2-Trichloroethyl 450 CN Pentachloroethyl 451 CN Cyclopropyl 452 CN Cyclobutyl 453 CN Cyclopenyl 454 CN Cyclohexyl 455 CN 1-Methylcyclopropyl 456 CN 2,2-Dimethylcyclopropyl 457 CN 1-Methylcyclohexyl 458 CN 2,2-Difluorocyclopropyl 459 CN 2,2-Dichlorocyclopropyl 460 CN 2,2-Dibromocyclopropyl 461 CN 2,2-Dichloro-3-Methylcyclopropyl 462 CN 2,2,3,3-Tetrafluorocyclobutyl 463 CN Ethenyl 464 CN 1-Propenyl 465 CN 2-Methyl-1-propenyl 466 CN 4-Methylpent-3-en-1-yl 467 CN 2-Propenyl 468 CN 2-Butenyl 469 CN 1-Methyl-2-propenyl 470 CN 3-Methyl-2-butenyl 471 CN 2,2-Difluoroethenyl 472 CN 2,2-Dichloroethenyl 473 CN 3,3,3-Trifluoropropenyl 474 CN 3,3,3-Trichloropropenyl 475 CN 3-Chloro-2-propenyl 476 CN Cyclopent-1-enyl 477 CN Cyclopentadienyl 478 CN Cyclohex-1-enyl 479 CN Pentafluorocyclopentadienyl 480 CN Pentachlorocyclopentadienyl 481 CN Styryl 482 CH₃ Methoxymethyl 483 CH₃ Ethoxymethyl 484 CH₃ n-Propoxymethyl 485 CH₃ iso-Propoxymethyl 486 CH₃ tert.-Butoxymethyl 487 CH₃ 2-Methoxyprop-2-yl 488 CH₃ 2-Ethoxyprop-2-yl 489 CH₃ 2-n-Propoxyprop-2-yl 490 CH₃ 2-iso-Propoxyprop-2-yl 491 CH₃ 2-tert.-Butoxyprop-2-yl 492 CH₃ Methylthiomethyl 493 CH₃ tert.-Butylthiomethyl 494 CH₃ 2-Methylthioprop-2-yl 495 CH₃ 2-iso-Propylthioprop-2-yl 496 CH₃ 2-tert.-Butylthioprop-2-yl 497 CH₃ Methyl m.p. 68-71° C.; IR (KBr): 1137, 1298, 1067, 1023, 1007, 771 498 CH₃ Ethyl 499 CH₃ n-Propyl 500 CH₃ iso-Propyl 501 CH₃ n-Butyl 502 CH₃ iso-Butyl 503 CH₃ sec.-Butyl 504 CH₃ tert.-Butyl 505 CH₃ n-Hexyl 506 CH₃ n-Decyl 507 CH₃ Cyclopropyl 508 CH₃ Cyclohexyl 509 CH₃ Phenylthiomethyl 510 CH₃ 2-Phenylthiomethyl 511 CH₃ 2-(2′-Chlorophenylthio)prop-2-yl) 512 CH₃ Ethynyl 513 CH₃ 1-Propynyl 514 CH₃ Methoxy 515 CH₃ Ethoxy 516 CH₃ n-Propoxy 517 CH₃ iso-Propoxy 518 CH₃ n-Butoxy 519 CH₃ iso-Butoxy 520 CH₃ sec.-Butoxy 521 CH₃ tert.-Butoxy 522 CH₃ Methylthio 523 CH₃ Ethylthio 524 CH₃ n-Propylthio 525 CH₃ iso-Propylthio 526 CH₃ n-Butylthio 527 CH₃ iso-Butylthio 528 CH₃ sec.-Butylthio 529 CH₃ tert.-Butylthio 530 CH₃ Benzylthio 531 CH₃ Trifluoromethoxy 532 CH₃ Cyano 533 CH₃ Amino 534 CH₃ Methylamino 535 CH₃ Dimethylamino 536 CH₃ Ethylamino 537 CH₃ Diethylamino 538 CH₃ Di-n-Propylamino 539 CH₃ Di-iso-Propylamino 540 CH₃ Di-n-Butylamino 541 CH₃ Di-iso-Butylamino 542 CH₃ Acetyl 543 CH₃ Propion-1-yl 544 CH₃ Butyr-1-yl 545 CH₃ iso-Butyr-1-yl 546 CH₃ Pivaloyl 547 CH₃ Benzoyl 548 CH₃ 4-Chlorobenzoyl 549 CH₃ Benzylcarbonyl 550 CH₃ Methoxycarbonyl 551 CH₃ Ethoxycarbonyl 552 CH₃ n-Propoxycarbonyl 553 CH₃ iso-Propoxycarbonyl 554 CH₃ n-Butoxycarbonyl 555 CH₃ iso-Butoxycarbonyl 556 CH₃ sec.-Butoxycarbonyl 557 CH₃ tert.-Butoxycarbonyl 558 CH₃ n-Hexoxycarbonyl 559 CH₃ Phenoxycarbonyl 560 CH₃ 4-Chlorophenoxycarbonyl 561 CH₃ Benzyloxycarbonyl 562 CH₃ Aminocarbonyl 563 CH₃ Dimethylaminocarbonyl 564 CH₃ Diethylaminocarbonyl 565 CH₃ Di-iso-Propylaminocarbonyl 566 CH₃ Phenylaminocarbonyl 567 CH₃ N-Methyl-N-Phenylaminocarbonyl 568 CH₃ Phenyl 569 CH₃ 2-Fluorophenyl m.p.: 89-91° C.; IR (KBr): 1732, 1071, 1012, 998, 768 570 CH₃ 3-Fluorophenyl m.p.: 83-85° C.; IR (KBr): 1724, 1204, 1067, 1031, 1015, 955 571 CH₃ 4-Fluorophenyl m.p.: 76-8° C.; IR (KBr): 1737, 1510, 1302, 1224, 1072, 1031, 1015, 933 572 CH₃ Pentafluorophenyl 573 CH₃ 2-Chlorophenyl 574 CH₃ 3-Chlorophenyl m.p.: 61-63° C.; IR (KBr): 1735, 1070, 1015, 1022, 785 575 CH₃ 4-Chlorophenyl oil; IR (film): 1708, 1634, 1256, 1129 576 CH₃ Pentachlorophenyl 577 CH₃ 2,3-Dichlorophenyl 578 CH₃ 2,4-Dichlorophenyl 579 CH₃ 2,5-Dichlorophenyl 580 CH₃ 2,6-Dichlorophenyl 581 CH₃ 3,4-Dichlorophenyl 582 CH₃ 3,5-Dichlorophenyl m.p.: 95-7° C.; IR (KBr): 1723, 1536, 1224, 1067, 1030, 1014, 937 583 CH₃ 2,3,4-Trichlorophenyl m.p.: 110-20° C.; 584 CH₃ 2,3,5-Trichlorophenyl 585 CH₃ 2,3,6-Trichlorophenyl 586 CH₃ 2,4,5-Trichlorophenyl 587 CH₃ 2,4,6-Tirchlorophenyl 588 CH₃ 3,4,5-Trichlorophenyl 589 CH₃ 2,3,4,6-Tetrachlorophenyl 590 CH₃ 2,3,5,6-Tetrachlorophenyl 591 CH₃ 2-Bromophenyl 592 CH₃ 3-Bromophenyl m.p.: 80-4° C.; IR (KBr): 1723, 1556, 1224, 1067, 1030, 1014, 957 593 CH₃ 4-Bromophenyl m.p.: 73-75° C.; IR (KBr): 1736, 1071, 1029, 1015, 932 594 CH₃ 2,4-Dibromophenyl 595 CH₃ 3-Bromo-4-fluorophenyl 596 CH₃ 3-Bromo-4-methoxyphenyl 597 CH₃ 2-Iodophenyl 598 CH₃ 3-Iodophenyl 599 CH₃ 4-Iodophenyl 600 CH₃ 2-Chloro-4-fluorophenyl 601 CH₃ 2-Chloro-5-fluorophenyl 602 CH₃ 2-Chloro-6-fluorophenyl 603 CH₃ 2-Chloro-4-bromophenyl 604 CH₃ 2-Bromo-4-chlorophenyl 605 CH₃ 2-Bromo-4-fluorophenyl 606 CH₃ 3-Bromo-4-chlorophenyl 607 CH₃ 3-Chloro-4-fluorophenyl 608 CH₃ 3-Fluoro-4-chlorophenyl 609 CH₃ 2-Cyanophenyl 610 CH₃ 3-Cyanophenyl 611 CH₃ 4-Cyanophenyl 612 CH₃ 2-Nitrophenyl 613 CH₃ 3-Nitrophenyl 614 CH₃ 4-Nitrophenyl m.p.: 88-90° C.; IR (KBr): 1725, 1512, 1342, 1219, 1068, 1009, 854 615 CH₃ 2-Methylphenyl 616 CH₃ 3-Methylphenyl m.p.: 93-96° C.; 617 CH₃ 4-Methylphenyl m.p.: 82-84° C.; IR (KBr): 1722, 1068, 1038, 1015, 920 618 CH₃ 2,4-Dimethylphenyl 619 CH₃ 2,6-Dimethylphenyl 620 CH₃ 3,4-Dimethylphenyl 621 CH₃ 3,5-Dimethylphenyl 622 CH₃ 2,3,4-Trimethylphenyl 623 CH₃ 2,3,5-Trimethylphenyl 624 CH₃ 2,3,6-Trimethylphenyl 625 CH₃ 2,4,5-Trimethylphenyl 626 CH₃ 2,4,6-Trimethylphenyl 627 CH₃ 3,4,5-Trimethylphenyl 628 CH₃ Pentamethylphenyl 629 CH₃ 2-Ethylphenyl 630 CH₃ 3-Ethylphenyl 631 CH₃ 4-Ethylphenyl 632 CH₃ 3,5-Diethylphenyl 633 CH₃ 2-n-Propylphenyl 634 CH₃ 3-n-Propylphenyl 635 CH₃ 4-n-Propylphenyl 636 CH₃ 2-iso-Propylphenyl 637 CH₃ 3-iso-Propylphenyl 638 CH₃ 4-iso-Propylphenyl 639 CH₃ 2,4-Di-iso-Propylphenyl 640 CH₃ 3,5-Di-iso-Propylphenyl 641 CH₃ 4-n-Butylphenyl 642 CH₃ 4-sec.-Butylphenyl 643 CH₃ 4-iso-Butylphenyl 644 CH₃ 4-tert.-Butylphenyl m.p. 45-50° C.; 645 CH₃ 3-tert.-Butylphenyl 646 CH₃ 2-tert.-Butylphenyl 647 CH₃ 2,4-Di-tert.-Butylphenyl 648 CH₃ 3,5-Di-tert.-Butylphenyl 649 CH₃ 4-n-Hexylphenyl 650 CH₃ 4-n-Dodecylphenyl 651 CH₃ 2-Methyl-4-tert.-Butylphenyl 652 CH₃ 2-Methyl-6-tert.-Butylphenyl 653 CH₃ 2-Methyl-4-iso-Propylphenyl 654 CH₃ 2-Methyl-4-Cyclohexylphenyl 655 CH₃ 2-Methyl-4-Phenylphenyl 656 CH₃ 2-Methyl-4-Benzylphenyl 657 CH₃ 2-Methyl-4-Phenoxyphenyl 658 CH₃ 2-Methyl-4-Benzyloxyphenyl 659 CH₃ 2-Methyl-3-Chlorophenyl 660 CH₃ 2-Methyl-4-Chlorophenyl 661 CH₃ 2-Methyl-5-Chlorophenyl 662 CH₃ 2-Methyl-6-chlorophenyl 663 CH₃ 2-Methyl-4-fluorophenyl 664 CH₃ 2-Methyl-3-bromophenyl 665 CH₃ 2-Methyl-4-bromophenyl 666 CH₃ 2-Methyl-3-methoxyphenyl 667 CH₃ 2-Methyl-4-methoxyphenyl 668 CH₃ 2-Methyl-5-methoxyphenyl 669 CH₃ 2-Methyl-6-methoxyphenyl 670 CH₃ 2-Methyl-4-iso-Propoxyphenyl 671 CH₃ 2-Methyl-2,5-dimethoxyphenyl 672 CH₃ 2-Methoxyphenyl m.p.: 74-6° C.; IR (KBr): 1741, 1433, 1295, 1249, 1224, 1067, 1022, 878 673 CH₃ 3-Methoxyphenyl 674 CH₃ 4-Methoxyphenyl m.p.: 89-91° C.; 675 CH₃ 2,3-Dimethoxyphenyl 676 CH₃ 2,4-Dimethoxyphenyl 677 CH₃ 2,5-Dimethoxyphenyl 678 CH₃ 2,6-Dimethoxyphenyl 679 CH₃ 3,4-Dimethoxyphenyl 680 CH₃ 3,5-Dimethoxyphenyl 681 CH₃ 3,6-Dimethoxyphenyl 682 CH₃ 2,3,4-Trimethoxyphenyl 683 CH₃ 2,3,5-Trimethoxyphenyl 684 CH₃ 2,3,6-Trimethoxyphenyl 685 CH₃ 2,4,5-Trimethoxyphenyl 686 CH₃ 2,4,6-Trimethoxyphenyl 687 CH₃ 3,4,5-Trimethoxyphenyl 688 CH₃ 2-Ethoxyphenyl 689 CH₃ 3-Ethoxyphenyl 690 CH₃ 4-Ethoxyphenyl 691 CH₃ 2-iso-Propoxyphenyl 692 CH₃ 3-iso-propoxyphenyl 693 CH₃ 4-iso-propoxyphenyl 694 CH₃ 3-tert.-Butoxyphenyl 695 CH₃ 4-tert.-Butoxyphenyl 696 CH₃ 2-Trifluoromethoxyphenyl 697 CH₃ 3-Trifluoromethoxyphenyl 698 CH₃ 4-Trifluoromethoxyphenyl 699 CH₃ 3-(1′,1′,2′,2′-Tetrafluoro)ethoxyphenyl 700 CH₃ 4-(1′,1′,2′,2′-Tetrafluoro)ethoxyphenyl 701 CH₃ 2-Chloromethylphenyl 702 CH₃ 3-Chloromethylphenyl 703 CH₃ 4-Chloromethylphenyl 704 CH₃ 2-Trifluoromethylphenyl m.p.: 78-80° C.; IR (KBr): 1741, 1315, 1116, 1068, 1010 705 CH₃ 3-Trifluoromethylphenyl m.p.: 70-72° C.; IR (KBr): 1740, 1297, 1281, 1164, 1124, 1073, 1010 706 CH₃ 4-Trifluoromethylphenyl m.p.: 57-58° C.; (IR (KBr): 1728, 1333, 1318, 1106, 1069, 986 707 CH₃ 2-(Methoxyiminomethyl)phenyl 708 CH₃ 3-(Methoxyiminomethyl)phenyl 709 CH₃ 4-(Methoxyiminomethyl)phenyl 710 CH₃ 2-(Ethoxyiminomethyl)phenyl 711 CH₃ 3-(Ethoxyiminomethyl)phenyl 712 CH₃ 4-(Ethoxyiminomethyl)phenyl 713 CH₃ 2-(n-Propoxyiminomethyl)phenyl 714 CH₃ 3-(n-Propoxyiminomethyl)phenyl 715 CH₃ 4-(n-Propoxyiminomethyl)phenyl 716 CH₃ 2-(iso-Propoxyiminomethyl)phenyl 717 CH₃ 3-(iso-Propoxyiminomethyl)phenyl 718 CH₃ 4-(iso-Propoxyiminomethyl)phenyl 719 CH₃ 2-(n-Butoxyiminomethyl)phenyl 720 CH₃ 3-(n-Butoxyiminomethyl)phenyl 721 CH₃ 4-(n-Butoxyiminomethyl)phenyl 722 CH₃ 2-(iso-Butoxyiminomethyl)phenyl 723 CH₃ 3-(iso-Butoxyiminomethyl)phenyl 724 CH₃ 4-(iso-Butoxyiminomethyl)phenyl 725 CH₃ 2-(tert.-Butoxyiminomethyl)phenyl 726 CH₃ 3-(tert.-Butoxyiminomethyl)phenyl 727 CH₃ 4-(tert.-Butoxyiminomethyl)phenyl 728 CH₃ 2-(n-Pentoxyiminomethyl)phenyl 729 CH₃ 3-(n-Pentoxyiminomethyl)phenyl 730 CH₃ 4-(n-Pentoxyiminomethyl)phenyl 731 CH₃ 2-(n-Hexoxyiminomethyl)phenyl 732 CH₃ 3-(n-Hexoxyiminomethyl)phenyl 733 CH₃ 4-(n-Hexoxyiminomethyl)phenyl 734 CH₃ 2-(Allyloxyiminomethyl)phenyl 735 CH₃ 3-(Allyloxyiminomethyl)phenyl 736 CH₃ 4-(Allyloxyiminomethyl)phenyl 737 CH₃ 2-(Benzyloxyiminomethyl)phenyl 738 CH₃ 3-(Benzyloxyiminomethyl)phenyl 739 CH₃ 4-(Benzyloxyiminomethyl)phenyl 740 CH₃ 2-(Methoxyimino-1′-ethyl)phenyl 741 CH₃ 3-(Methoxyimino-1′-ethyl)phenyl 742 CH₃ 4-(Methoxyimino-1′-ethyl)phenyl 743 CH₃ 2-(Ethoxyimino-1′-ethyl)phenyl 744 CH₃ 3-(Ethoxyimino-1′-ethyl)phenyl 745 CH₃ 4-(Ethoxyimino-1′-ethyl)phenyl 746 CH₃ 2-(n-Propoxyimino-1′-ethyl)phenyl 747 CH₃ 3-(n-Propoxyimino-1′-ethyl)phenyl 748 CH₃ 4-(n-Propoxyimino-1′-ethyl)phenyl 749 CH₃ 2-(n-Butoxyamino-1′-ethyl)phenyl 750 CH₃ 3-(n-Butoxyamino-1′-ethyl)phenyl 751 CH₃ 4-(n-Butoxyamino-1′-ethyl)phenyl 752 CH₃ 2-(n-Pentoxyimino-1′-ethyl)phenyl 753 CH₃ 3-(n-Pentoxyimino-1′-ethyl)phenyl 754 CH₃ 4-(n-Pentoxyimino-1′-ethly)phenyl 755 CH₃ 2-(n-Hexoxyimino-1′-ethyl)phenyl 756 CH₃ 3-(n-Hexoxyimino-1′-ethyl)phenyl 757 CH₃ 4-(n-Hexoxyimino-1′-ethyl)phenyl 758 CH₃ 2-(Allyloxyimino-1′-ethyl)phenyl 759 CH₃ 3-(Allyloxyimino-1′-ethyl)phenyl 760 CH₃ 4-(Allyloxyimino-1′-ethyl)phenyl 761 CH₃ 2-(Benzyloxyimino-1′-ethyl)phenyl 762 CH₃ 3-(Benzyloxyimino-1′-ethyl)phenyl 763 CH₃ 4-(Benzyloxyimino-1′-ethyl)phenyl 764 CH₃ 2-Phenylphenyl 765 CH₃ 3-Phenylphenyl 766 CH₃ 4-Phenylphenyl 767 CH₃ 2-Phenoxyphenyl 768 CH₃ 3-Phenoxyphenyl 769 CH₃ 4-Phenoxyphenyl m.p.: 91-3° C.; IR (KBr): 1732, 1587, 1491, 1241, 1071, 1014, 995, 769 770 CH₃ 2-Benzyloxyphenyl 771 CH₃ 3-Benzyloxyphenyl 772 CH₃ 4-Benzyloxyphenyl 773 CH₃ 4-(Imidazol-1′-yl)phenyl 774 CH₃ 4-(Piperazin-1′-yl)phenyl 775 CH₃ 4-(Morpholin-1′-yl)phenyl 776 CH₃ 4-(Piperadin-1′-yl)phenyl 777 CH₃ 4-(Pyridyl-2′-oxy)phenyl 778 CH₃ 2-Cyclopropylphenyl 779 CH₃ 3-Cyclopropylphenyl 780 CH₃ 4-Cyclopropylphenyl 781 CH₃ 3-Cyclohexylphenyl 782 CH₃ 4-Cyclohexylphenyl m.p.: 53-5° C.; 783 CH₃ 4-Oxiramylphenyl 784 CH₃ 4-(1′,3′-Dioxan-2′-yl)phenyl 785 CH₃ 4-(Tetrahydropyro-2-yloxy)phenyl 786 CH₃ 1-Naphthyl 787 CH₃ 2-Naphthyl 788 CH₃ 9-Anthryl 789 CH₃ 1-Naphthoxy 790 CH₃ 2-Naphthoxy 791 CH₃ 9-Anthroxy 792 CH₃ Phenoxy 793 CH₃ 2-Chlorophenoxy 794 CH₃ 3-Chlorophenoxy 795 CH₃ 4-Chlorophenoxy 796 CH₃ 4-Methylphenoxy 797 CH₃ 4-tert.-Butylphenoxy 798 CH₃ 4-Methoxyphenoxy 799 CH₃ 4-Ethoxyphenoxy 800 CH₃ 4-tert.-Butoxyphenoxy 801 CH₃ Phenylthio 802 CH₃ 2-Chlorophenylthio 803 CH₃ 4-Chlorophenylthio 804 CH₃ Benzyl 805 CH₃ 2-Methylbenzyl 806 CH₃ 3-Methylbenzyl 807 CH₃ 4-Methylbenzyl 808 CH₃ 4-tert.-Butylbenzyl 809 CH₃ 2-Chlorobenzyl 810 CH₃ 3-Chlorobenzyl 811 CH₃ 4-Chlorobenzyl 812 CH₃ 2,4-Dichlorobenzyl 813 CH₃ 2,6-Dichlorobenzyl 814 CH₃ 2,4,6-Trichlorobenzyl 815 CH₃ 2-Trifluoromethylbenzyl 816 CH₃ 3-Trifluoromethylbenzyl 817 CH₃ 4-Trifluoromethylbenzyl 818 CH₃ 2-Methoxybenzyl 819 CH₃ 4-Methoxybenzyl 820 CH₃ 4-tert.-Butoxybenzyl 821 CH₃ 4-Phenoxybenzyl 822 CH₃ 1-Phenethyl 823 CH₃ 2-Phenethyl 824 CH₃ 1-Phenylpropyl 825 CH₃ 2-Phenylpropyl 826 CH₃ 3-Phenylpropyl 827 CH₃ 2-Methyl-2-phenylpropyl 828 CH₃ 2-Methyl-3-phenylpropyl 829 CH₃ 4-Phenylbutyl 830 CH₃ 2-Phenyl-1-ethenyl 831 CH₃ 1-Phenyl-1-ethenyl 832 CH₃ 1-Phenyl-1-propenyl 833 CH₃ 1-Phenyl-1-propen-2-yl 834 CH₃ 2,2-Diphenylethenyl 835 CH₃ Phenoxymethyl 836 CH₃ 2-Pyridyl 837 CH₃ 3-Pyridyl 838 CH₃ 4-Pyridyl 839 CH₃ 2,6-Pyrimidinyl 840 CH₃ 1,5-Pyrimidinyl 841 CH₃ 2-Thienyl 842 CH₃ 3-Thienyl 843 CH₃ 2-Furyl 844 CH₃ 3-Furyl 845 CH₃ 1-Pyrrolyl 846 CH₃ 1-Imidazolyl 847 CH₃ 1,2,4-Triazolyl 848 CH₃ 1,3,4-Triazolyl 849 CH₃ 4-Thiazolyl 850 CH₃ 2-Benzothiazolyl 851 CH₃ 2-Pyridyloxy 852 CH₃ 2-Pyrimidiayloxy 853 CH₃ 2-Pyridylthio 854 CH₃ 2-Pyrimidinylthio 855 CH₃ 2-Benzothiazolythio 856 CH₃ Phenylthiomethyl 857 CH₃ 2-Pyridylmethyl 858 CH₃ 3-Pyridylmethyl 859 CH₃ Furfuryloxy 860 CH₃ Thienylmethoxy 861 CH₃ 3-Isoxazolylmethoxy 862 CH₃ 2-Oxoxazolymethoxy 863 CH₃ 2-Pyridylmethoxy 864 CH₃ 2′-Furyl-2-ethenyl 865 CH₃ 2′-Thienyl-2-ethenyl 866 CH₃ 3′-Pyridyl-2-ethenyl 867 CH₃ Oxinanyl 868 CH₃ 1-Azinidinyl 869 CH₃ 1-Azinidinyl 870 CH₃ 1-Pyrrolidinyl 871 CH₃ 2-Tetrahydrofuryl 872 CH₃ 2-Tetrahydropyranyl 873 CH₃ 3-Tetrahydropyranyl 874 CH₃ 1-Piperdinyl 875 CH₃ 1-Morpholinyl 876 CH₃ 1-Piperezinyl 877 CH₃ 1,3-Dioxan-2-yl 878 CH₃ 3-Tetrahydrothiopyranyl 879 CH₃ 2-Dihydropyranyloxy 880 CH₃ 2-Tetrahydropyranyloxy 881 CH₃ CF₃ 882 CH₃ 2-Fluoroethyl 883 CH₃ 2,2,2-Trifluoroethyl 884 CH₃ Pentafluoroethyl 885 CH₃ Chloromethyl 886 CH₃ Dichloromethyl 887 CH₃ Trichloromethyl 888 CH₃ 2-Chloroethyl 889 CH₃ 2,2,2-Trichloromethyl 890 CH₃ Pentachloroethyl 891 CH₃ Cyclopropyl 892 CH₃ Cyclobutyl 893 CH₃ Cyclopentyl 894 CH₃ Cyclohexyl 895 CH₃ 1-Methylcyclopropyl 896 CH₃ 2,2-Dimethylcyclopropyl 897 CH₃ 1-Methylcyclohexyl 898 CH₃ 2,2-Difluorocyclopropyl 899 CH₃ 2,2-Dichlorocyclopropyl 900 CH₃ 2,2-Dibromocyclopropyl 901 CH₃ 2,2-Dichloro-3-Methylcyclopropyl 902 CH₃ 2,2,3,3-Tetrafluorocyclobutyl 903 CH₃ Ethenyl 904 CH₃ 1-Propenyl 905 CH₃ 2-Methyl-1-propenyl 906 CH₃ 4-Methylpent-3-en-1-yl 907 CH₃ 2-Propenyl 908 CH₃ 2-Bucanyl 909 CH₃ 1-Methyl-2-propenyl 910 CH₃ 3-Methyl-2-butenyl 911 CH₃ 2,2-Difluoroethenyl 912 CH₃ 2,2-Dichloroethenyl 913 CH₃ 3,3,3-Trifluoropropenyl 914 CH₃ 3,3,3-Trichloropropenyl 915 CH₃ 3-Chloro-2-propenyl 916 CH₃ Cyclopent-1-enyl 917 CH₃ Cyclopentadienyl 918 CH₃ Cyclohex-1-enyl 919 CH₃ Pentafluorocyclopentadienyl 920 CH₃ Pentachlorocyclopentadienyl 921 Phenyl Phenyl 922 Phenyl 2-Fluorophenyl 923 Phenyl 4-Fluorophenyl 924 Phenyl 2-Chlorophenyl 925 Phenyl 3-Chlorophenyl 926 Phenyl 4-Chlorophenyl 927 Phenyl 3,4-Dichlorophenyl 928 Phenyl 4-Nitrophenyl 929 Phenyl 2-CF₃-Phenyl 930 Phenyl 3-CF₃-Phenyl 931 Phenyl 4-CF₃-Phenyl 932 Phenyl 2-Methylphenyl 933 Phenyl 3-Methylphenyl 934 Phenyl 4-Methylphenyl 935 Phenyl 2,4-Dimethylphenyl 936 Phenyl 4-tert.-Butylphenyl 937 Phenyl 4-Methoxyphenyl 938 4-Fluorophenyl 4-Fluorophenyl 939 2-Fluorophenyl 4-Fluorophenyl 940 2-Chlorophenyl 4-Fluorophenyl 941 2-Chlorophenyl 2-Chlorophenyl 942 3-Chlorophenyl 3-Chlorophenyl 943 4-Chlorophenyl 4-Chlorophenyl 944 2-Chlorophenyl 4-Chlorophenyl 945 4-Methoxyphenyl 4-Methoxyphenyl 946 4-Dimethylaminophenyl 4-Dimethylaminophenyl 947 Phenyl Naphethyl 948 Ethyl Ethyl 949 Ethyl n-Propyl 950 Ethyl iso-Propyl 951 Ethyl n-Butyl 952 Ethyl iso-Butyl 953 Ethyl 2-Methyl-butyl 954 Ethyl Benzyl 955 n-Propyl n-Propyl 956 iso-Propyl iso-Propyl 957 n-Butyl n-Butyl 958 iso-Butyl iso-Butyl 959 tert.-Butyl tert.-Butyl 960 Benzyl Benzyl 961 Pentachloroethyl Pentachloroethyl 962 n-Hexyl n-Hexyl 963 Ethoxycarbonyl Ethoxycarbonyl 964 Phenyl Benzoyl 965 Ethyl Phenyl 966 N-Butyl Phenyl 967 Styryl Styryl 968 2-Pyridyl 2-Pyridyl 969 3-Pyridyl 3-Pyridyl 970 Ethyl 2-Pyridyl m.p.: 84-86° C.; 971

m.p.: 103-105° C.;

TABLE III

No. X Y R¹ R² = H R³ R⁴ Data 1 CHS—CH₃ O CH₃ CF₃ Phenyl 2 CHS—CH₃ O CH₃ Cyclopropyl Phenyl 3 CHS—CH₃ O CH₃ Cyclopropyl 4-Chlorophenyl 4 CHS—CH₃ O CH₃ Cyclopropyl 4-Methoxyphenyl 5 CHS—CH₃ O CH₃ Cyclopropyl 4-tert.-butylphenyl 6 CHS—CH₃ O CH₃ CN Methylthio 7 CHS—CH₃ O CH₃ CN 2-Methoxyprop-2-yl 8 CHS—CH₃ O CH₃ CN 2-Methylthioprop-2-yl 9 CHS—CH₃ O CH₃ CN Phenylthio 10 CHS—CH₃ O CH₃ CN iso-Propyl 11 CHS—CH₃ O CH₃ CN CN 12 CHS—CH₃ O CH₃ CN Acetyl 13 CHS—CH₃ O CH₃ CN Benzoyl 14 CHS—CH₃ O CH₃ CN Methoxycarbonyl 15 CHS—CH₃ O CH₃ CN Phenyl 16 CHS—CH₃ O CH₃ CN 2-Chlorophenyl 17 CHS—CH₃ O CH₃ CN 4-Chlorophenyl 18 CHS—CH₃ O CH₃ CN 2-Methylphenyl 19 CHS—CH₃ O CH₃ CN 4-tert.-butylphenyl 20 CHS—CH₃ O CH₃ CN 4-n-Butoxyiminomethyl)phenyl 21 CHS—CH₃ O CH₃ CN 2-Pyridyl 22 CHS—CH₃ O CH₃ CN Styryl 23 CHS—CH₃ O CH₃ CN 1-Propenyl 24 CHS—CH₃ O CH₃ CH₃ Phenylthio 25 CHS—CH₃ O CH₃ CH₃ Benzyl 26 CHS—CH₃ O CH₃ CH₃ tert.-Butyl 27 CHS—CH₃ O CH₃ CH₃ iso-Propyl 28 CHS—CH₃ O CH₃ CH₃ 2-Methylbutyl 29 CHS—CH₃ O CH₃ CH₃ iso-Butyl 30 CHS—CH₃ O CH₃ CH₃ Phenyl 31 CHS—CH₃ O CH₃ CH₃ 2-Chlorophenyl 32 CHS—CH₃ O CH₃ CH₃ 4-Chlorophenyl 33 CHS—CH₃ O CH₃ CH₃ 2-Methylphenyl 34 CHS—CH₃ O CH₃ CH₃ Naphthyl 35 CHS—CH₃ O CH₃ CH₃ 1-Pyridyl 36 CHS—CH₃ O CH₃ iso-Butyl iso-Butyl 37 CHS—CH₃ O CH₃ Phenyl Phenyl 38 CHS—CH₃ O CH₃ CH₂CH₂CH₂CH₂ 39 CHS—CH₃ O CH₃ CH₂CH₂CH₂CH₂CH₂ 40 CH—CH₃ O CH₃ CF₃ Phenyl 41 CH—CH₃ O CH₃ Cyclopropyl Phenyl 42 CH—CH₃ O CH₃ Cyclopropyl 4-Chlorophenyl 43 CH—CH₃ O CH₃ Cyclopropyl 4-Methoxyphenyl 44 CH—CH₃ O CH₃ Cyclopropyl 4-tert.-butylphenyl 45 CH—CH₃ O CH₃ CN Methylthio 46 CH—CH₃ O CH₃ CN 2-Methoxyprop-2-yl IR (film): 1717, 1436, 1367, 1256, 1210, 1179, 1070, 1037, 1009, 759 47 CH—CH₃ O CH₃ CN 2-Methylthioprop-2-yl ¹H-NMR (CDCl₃): δ = 1.45s, 1.6d, 1.8s, 3.7s, 5.1s, 7.1-7.5m 48 CH—CH₃ O CH₃ CN Phenylthio 49 CH—CH₃ O CH₃ CN iso-Propyl ¹H-NMR (CDCl₃): δ = 1.2d, 1.6d, 2.7m, 3.67s, 5.1s, 7.0-7.5m 50 CH—CH₃ O CH₃ CN CN 51 CH—CH₃ O CH₃ CN Acetyl 52 CH—CH₃ O CH₃ CN Benzoyl 53 CH—CH₃ O CH₃ CN Methoxycarbonyl 54 CH—CH₃ O CH₃ CN Phenyl ¹H-NMR (CDCl₃): δ = 1.6d, 3.7s, 5.2s, 7.0-1.8m 55 CH—CH₃ O CH₃ CN 2-Chlorophenyl 56 CH—CH₃ O CH₃ CN 4-Chlorophenyl 57 CH—CH₃ O CH₃ CN 2-Methylphenyl 58 CH—CH₃ O CH₃ CN 4-tert.-butylphenyl 59 CH—CH₃ O CH₃ CN 4-(n-Butoxyiminomethyl)phenyl 60 CH—CH₃ O CH₃ CN 2-Pyridyl 61 CH—CH₃ O CH₃ CN Styryl 62 CH—CH₃ O CH₃ CN 1-Propenyl 63 CH—CH₃ O CH₃ CH₃ Phenylthio 64 CH—CH₃ O CH₃ CH₃ Benzyl 65 CH—CH₃ O CH₃ CH₃ tert.-Butyl 66 CH—CH₃ O CH₃ CH₃ iso-Propyl 67 CH—CH₃ O CH₃ CH₃ 2-Methylbutyl 68 CH—CH₃ O CH₃ CH₃ iso-Butyl 69 CH—CH₃ O CH₃ CH₃ Phenyl 70 CH—CH₃ O CH₃ CH₃ 2-Chlorophenyl 71 CH—CH₃ O CH₃ CH₃ 4-Chlorophenyl IR (film): 1716, 1490, 1434, 1253, 1206, 1096, 1036, 1012, 820, 760 72 CH—CH₃ O CH₃ CH₃ 2-Methylphenyl 73 CH—CH₃ O CH₃ CH₃ Naphthyl 74 CH—CH₃ O CH₃ CH₃ 1-Pyridyl 75 CH—CH₃ O CH₃ iso-Butyl iso-Butyl 76 CH—CH₃ O CH₃ Phenyl Phenyl 77 CH—CH₃ O CH₃ CH₂CH₂CH₂CH₂ 78 CH—CH₃ O CH₃ CH₂CH₂CH₂CH₂CH₂ 79 CH₂ O CH₃ CF₃ Phenyl 80 CH₂ O CH₃ Cyclopropyl Phenyl 81 CH₂ O CH₃ Cyclopropyl 4-Chlorophenyl 82 CH₂ O CH₃ Cyclopropyl 4-Methoxyphenyl 83 CH₂ O CH₃ Cyclopropyl 4-tert.-butylphenyl 84 CH₂ O CH₃ CN Methylthio 85 CH₂ O CH₃ CN 2-Methoxyprop-2-yl 86 CH₂ O CH₃ CN 2-Methylthioprop-2-yl 87 CH₂ O CH₃ CN Phenylthio 88 CH₂ O CH₃ CN iso-Propyl 89 CH₂ O CH₃ CN CN 90 CH₂ O CH₃ CN Acetyl 91 CH₂ O CH₃ CN Benzoyl 92 CH₂ O CH₃ CN Methoxycarbonyl 93 CH₂ O CH₃ CN Phenyl 94 CH₂ O CH₃ CN 2-Chlorophenyl 95 CH₂ O CH₃ CN 4-Chlorophenyl 96 CH₂ O CH₃ CN 2-Methylphenyl 97 CH₂ O CH₃ CN 4-tert.-butylphenyl 98 CH₂ O CH₃ CN 4-(n-Butoxyiminomethyl)phenyl 99 CH₂ O CH₃ CN 2-Pyridyl 100 CH₂ O CH₃ CN Styryl 101 CH₂ O CH₃ CN 1-Propenyl 102 CH₂ O CH₃ CH₃ Phenylthio 103 CH₂ O CH₃ CH₃ Benzyl 104 CH₂ O CH₃ CH₃ tert.-Butyl 105 CH₂ O CH₃ CH₃ iso-Propyl 106 CH₂ O CH₃ CH₃ 2-Methylbutyl 107 CH₂ O CH₃ CH₃ iso-Butyl 108 CH₂ O CH₃ CH₃ Phenyl 109 CH₂ O CH₃ CH₃ 2-Chlorophenyl 110 CH₂ O CH₃ CH₃ 4-Chlorophenyl 111 CH₂ O CH₃ CH₃ 2-Methylphenyl 112 CH₂ O CH₃ CH₃ Naphthyl 113 CH₂ O CH₃ CH₃ 1-Pyridyl 114 CH₂ O CH₃ iso-Butyl iso-Butyl 115 CH₂ O CH₃ Phenyl Phenyl 116 CH₂ O CH₃ CH₂CH₂CH₂CH₂ 117 CH₂ O CH₃ CH₂CH₂CH₂CH₂CH₂ 118 N—OCH₃ S CH₃ CF₃ Phenyl 119 N—OCH₃ S CH₃ Cyclopropyl Phenyl 120 N—OCH₃ S CH₃ Cyclopropyl 4-Chlorophenyl 121 N—OCH₃ S CH₃ Cyclopropyl 4-Methoxyphenyl 122 N—OCH₃ S CH₃ Cycloproyl 4-tert.-butylphenyl 123 N—OCH₃ S CH₃ CN Methylthio 124 N—OCH₃ S CH₃ CN 2-Methoxyprop-2-yl 125 N—OCH₃ S CH₃ CN 2-Methylthioprop-2-yl 126 N—OCH₃ S CH₃ CN Phenylthio 127 N—OCH₃ S CH₃ CN iso-Propyl 128 N—OCH₃ S CH₃ CN CN 129 N—OCH₃ S CH₃ CN Acetyl 130 N—OCH₃ S CH₃ CN Benzoyl 131 N—OCH₃ S CH₃ CN Methoxycarbonyl 132 N—OCH₃ S CH₃ CN Phenyl 133 N—OCH₃ S CH₃ CN 2-Chlorophenyl 134 N—OCH₃ S CH₃ CN 4-Chlorophenyl 135 N—OCH₃ S CH₃ CN 2-Methylphenyl 136 N—OCH₃ S CH₃ CN 4-tert.-butylphenyl 137 N—OCH₃ S CH₃ CN 4-(n-Butoxyiminomethyl)phenyl 138 N—OCH₃ S CH₃ CN 2-Pyridyl 139 N—OCH₃ S CH₃ CN Styryl 140 N—OCH₃ S CH₃ CN 1-Propenyl 141 N—OCH₃ S CH₃ CH₃ Phenylthio 142 N—OCH₃ S CH₃ CH₃ Benzyl 143 N—OCH₃ S CH₃ CH₃ tert.-Butyl 144 N—OCH₃ S CH₃ CH₃ iso-Propyl 145 N—OCH₃ S CH₃ CH₃ 2-Methylbutyl 146 N—OCH₃ S CH₃ CH₃ iso-Butyl 147 N—OCH₃ S CH₃ CH₃ Phenyl 148 N—OCH₃ S CH₃ CH₃ 2-Chlorophenyl 149 N—OCH₃ S CH₃ CH₃ 4-Chlorophenyl 150 N—OCH₃ S CH₃ CH₃ 2-Methylphenyl 151 N—OCH₃ S CH₃ CH₃ Naphthyl 152 N—OCH₃ S CH₃ CH₃ 1-Pyridyl 153 N—OCH₃ S CH₃ iso-butyl iso-Butyl 154 N—OCH₃ S CH₃ Phenyl Phenyl 155 N—OCH₃ S CH₃ CH₂CH₂CH₂CH₂ 156 N—OCH₃ S CH₃ CH₂CH₂CH₂CH₂CH₂ 157 N—OCH₃ NH CH₃ CF₃ Phenyl 158 N—OCH₃ NH CH₃ Cyclopropyl Phenyl 159 N—OCH₃ NH CH₃ Cyclopropyl 4-Chlorophenyl m.p.: 71-74° C. IR (KBr): 3348, 1663, 1529, 1042, 1030, 982 160 N—OCH₃ NH CH₃ Cyclopropyl 4-Methoxyphenyl 161 N—OCH₃ NH CH₃ Cyclopropyl 4-tert.-butylphenyl 162 N—OCH₃ NH CH₃ CN Methylthio 163 N—OCH₃ NH CH₃ CN 2-Methoxyprop-2-yl 164 N—OCH₃ NH CH₃ CN 2-Methylthioprop-2-yl 165 N—OCH₃ NH CH₃ CN Phenylthio 166 N—OCH₃ NH CH₃ CN iso-Propyl 167 N—OCH₃ NH CH₃ CN CN 168 N—OCH₃ NH CH₃ CN Acetyl 169 N—OCH₃ NH CH₃ CN Benzoyl 170 N—OCH₃ NH CH₃ CN Methoxycarbonyl 171 N—OCH₃ NH CH₃ CN Phenyl 172 N—OCH₃ NH CH₃ CN 2-Chlorophenyl 173 N—OCH₃ NH CH₃ CN 4-Chlorophenyl 174 N—OCH₃ NH CH₃ CN 2-Methylphenyl 175 N—OCH₃ NH CH₃ CN 4-tert.-butylphenyl 176 N—OCH₃ NH CH₃ CN 4-(n-Butoxyiminomethyl)phenyl 177 N—OCH₃ NH CH₃ CN 2-Pyridyl 178 N—OCH₃ NH CH₃ CN Styryl 179 N—OCH₃ NH CH₃ CN 1-Propenyl 180 N—OCH₃ NH CH₃ CH₃ Phenylthio 181 N—OCH₃ NH CH₃ CH₃ Benzyl 182 N—OCH₃ NH CH₃ CH₃ tert.-Butyl 183 N—OCH₃ NH CH₃ CH₃ iso-Propyl 184 N—OCH₃ NH CH₃ CH₃ 2-Methylbutyl 185 N—OCH₃ NH CH₃ CH₃ iso-Butyl 186 N—OCH₃ NH CH₃ CH₃ Phenyl 187 N—OCH₃ NH CH₃ CH₃ 2-Chlorophenyl 188 N—OCH₃ NH CH₃ CH₃ 4-Chlorophenyl m.p.: 119-121° C. IR (KBr): 3421, 1676, 1037, 985, 933, 752 189 N—OCH₃ NH CH₃ CH₃ 2-Methylphenyl No. X Y R¹ R² R³ R⁴ Data 190 N—OCH₃ NH CH₃ H CH₃ Naphthyl 191 N—OCH₃ NH CH₃ H CH₃ 1-Pyridyl 192 N—OCH₃ NH CH₃ H iso-Butyl iso-Butyl 193 N—OCH₃ NH CH₃ H Phenyl Phenyl 194 N—OCH₃ NH CH₃ H CH₂CH₂CH₂CH₂ 195 N—OCH₃ NH CH₃ H CH₂CH₂CH₂CH₂CH₂ 196 N—OCH₃ O C₂H₅ H CH₃ Phenyl 197 CH—OCH₃ O C₂H₅ H CH₃ Phenyl 198 N—OCH₃ O n-C₃H₅ H CH₃ Phenyl 199 CHOCH₃ O n-C₃H₅ H CH₃ Phenyl 200 CHC₂H₅ O CH₃ H CH₃ Phenyl 201 N—OCH₃ O CH₃ CH₃ CH₃ Phenyl 202 CHOCH₃ O CH₃ CH₃ CH₃ Phenyl 203 N—OCH₃ O CH₃ CH₃ CN Phenyl 204 CHOCH₃ O CH₃ CH₃ CN Phenyl 205 CHS—CH₃ O CH₃ H H Phenyl 206 CH—CH₃ O CH₃ H H Phenyl 207 CH₂ O CH₃ H H Phenyl 208 NOCH₃ S CH₃ H H Phenyl 209 CHOCH₃ S CH₃ H H Phenyl 210 CHOCH₃ NH CH₃ H H Phenyl 211 NOCH₃ NH CH₃ H H Phenyl 212 CH—OCH₃ S CH₃ H CN Methylthio No. X Y R¹ R² = H R³ R⁴ Data 213 CH—OCH₃ S CH₃ CN 2-Methoxyprop-2-yl 214 CH—OCH₃ S CH₃ CN 2-Methylthioprop-2-yl 215 CH—OCH₃ S CH₃ CN Phenylthio 216 CH—OCH₃ S CH₃ CN iso-Propyl 217 CH—OCH₃ S CH₃ CN CN 218 CH—OCH₃ S CH₃ CN Acetyl 219 CH—OCH₃ S CH₃ CN Benzoyl 220 CH—OCH₃ S CH₃ CN Methoxycarbonyl 221 CH—OCH₃ S CH₃ CN Phenyl 222 CH—OCH₃ S CH₃ CN 2-Chlorophenyl 223 CH—OCH₃ S CH₃ CN 4-Chlorophenyl 224 CH—OCH₃ S CH₃ CN 2-Methylphenyl 225 CH—OCH₃ S CH₃ CN 4-tert.-butylphenyl 226 CH—OCH₃ S CH₃ CN 4-(n-Butoxyiminomethyl)phenyl 227 CH—OCH₃ S CH₃ CN 2-Pyridyl 228 CH—OCH₃ S CH₃ CN Styryl 229 CH—OCH₃ S CH₃ CN 1-Propenyl 230 CH—OCH₃ S CH₃ CN Methylthio 231 CH—OCH₃ NH CH₃ CN 2-Methoxyprop-2-yl 232 CH—OCH₃ NH CH₃ CN 2-Methylthioprop-2-yl 233 CH—OCH₃ NH CH₃ CN Phenylthio 234 CH—OCH₃ NH CH₃ CN iso-Propyl 235 CH—OCH₃ NH CH₃ CN CN 236 CH—OCH₃ NH CH₃ CN Acetyl 237 CH—OCH₃ NH CH₃ CN Benzoyl 238 CH—OCH₃ NH CH₃ CN Methoxycarbonyl 239 CH—OCH₃ NH CH₃ CN Phenyl 240 CH—OCH₃ NH CH₃ CN 2-Chlorophenyl 241 CH—OCH₃ NH CH₃ CN 4-Chlorophenyl 242 CH—OCH₃ NH CH₃ CN 2-Methylphenyl 243 CH—OCH₃ NH CH₃ CN 4-tert.-butylphenyl 244 CH—OCH₃ NH CH₃ CN 4-(n-Butoxyiminomethyl)phenyl 245 CH—OCH₃ NH CH₃ CN 2-Pyridyl 246 CH—OCH₃ NH CH₃ CN Styryl 247 CH—OCH₃ NH CH₃ CN 1-Propenyl 248 N—OCH₃ NH CH₃ CH₃ 3-Chlorophenyl m.p.: 71-74° C. 249 N—OCH₃ NH CH₃ CH₃ 3,5-Dichlorophenyl m.p.: 94-97° C. 250 N—OCH₃ NH CH₃ CH₃ 2,3,4-Trichlorophenyl m.p.: 110-112° C. 251 N—OCH₃ NH CH₃ CH₃ 3-Bromophenyl m.p.: 74-77° C. 252 N—OCH₃ NH CH₃ CH₃ 4-Methylphenyl m.p.: 69-72° C. 253 N—OCH₃ NH CH₃ CH₃ 4-Nitrophenyl m.p.: 134-137° C. 254 CH—CH₃ O CH₃ CN 2-Ethoxy-prop-2-yl IR (film): 2982, 1717, 1436, 1255, 1210, 1192, 1067, 1037, 1010 255 CH—CH₃ O CH₃ CN 2-i-Propoxy-prop-2-yl IR (film): 2983, 1718, 1383, 1370, 1255, 1173, 1119, 1109, 1037, 1002 256 CH—CH₃ O CH₃ CN 2-n-Butyoxy-prop-2-yl IR (film): 2957, 1718, 1435, 1255, 1176, 1036, 1010, 759 257 CH—CH₃ O CH₃ CN 2-i-Butyoxy-prop-2-yl IR (film): 2956, 1717, 1435, 1366, 1255, 1209, 1176, 1064, 1037, 1008 258 CH—CH₃ O CH₃ CN Cyclopropyl ¹H-NMR (CDCl₃): δ = 0.9m, 1.6d, 2.3m, 3.67s, 5.15s, 7.05-7.4m 259 CH—CH₃ O CH₃ CN 2-Ethylthio-prop-2-yl ¹H-NMR (CDCl₃): δ = 1.1t, 1,5s, 1.6d, 2.2q, 3.7s, 5.1s, 7.1-7.5m 260 CH—CH₃ O CH₃ CN 2-i-Propylthio-pro-2-yl ¹H-NMR (CDCl₃): δ = 1.15s, 1.5s, 1.6d, 2.6m, 3.7s, 5.1s, 7.1-7.5m 261 CH—CH₃ O CH₃ CN 2-Tetrahydropyranyl ¹H-NMR (CDCl₃): δ = 1.4-1.9m, 1.6d, 3.5m, 3.7s, 4.1m, 5.1s, 7.0-7.5m

TABLE IV

No. X Y R¹ R³ R⁴ Data 1 CH—OCH₃ O CH₃ CH₃ Phenyl 2 CH—OCH₃ O CH₃ CH₃ 3-Bromophenyl 3 CH—OCH₃ O CH₃ CH₃ 4-Phenoxyphenyl 4 CH—OCH₃ O CH₃ CH₃ 4-Cyclohexylphenyl 5 NOCH₃ O CH₃ CH₃ Phenyl 6 NOCH₃ O CH₃ CH₃ 3-Bromophenyl oil: IR (film): 1727, 1436, 1312, 1240, 1032 7 NOCH₃ O CH₃ CH₃ 4-Phenoxyphenyl oil: IR (film): 1727, 1489, 1239, 1031, 683 8 NOCH₃ O CH₃ CH₃ 4-Cyclohexylphenyl oil: IR (film): 2925, 1728, 1447, 1239, 1164, 1077, 1032 9 CHOCH₃ O CH₃ CN iso-Propyl 2970, 2220, 1710, 1127 10 CHOCH₃ O CH₃ CN 2-Methoxyprop-2-yl oil: IR (film): 2980, 2220, 1710, 1127 11 CHOCH₃ O CH₃ CN 2-Methylthioprop-2-yl oil: IR (film): 2980, 2220, 1709, 1127 12 CHOCH₃ O CH₃ CN 2-Tetrahydrofuranyl oil: IR (film): 2945, 2850, 2220, 1709, 1127 13 CHOCH₃ O CH₃ CN Phenyl oil: IR (film): 2940, 2220, 1709, 1127, 1030

TABLE V

No. R³ R⁴ Data 1 H H 2 H Methoxymethyl 3 H Ethoxymethyl 4 H n-Propoxymethyl 5 H iso-Propoxymethyl 6 H tert.-Butoxymethyl 7 H 2-Methoxyprop-2-yl 8 H 2-Ethoxyprop-2-yl 9 H 2-n-Propoxyprop-2-yl 10 H 2-iso-Propoxyprop-2-yl 11 H 2-tert.-Butoxyprop-2-yl 12 H Methylthiomethyl 13 H tert.-Butylthioprop-2-yl 14 H 2-Methylthioprop-2-yl 15 H 2-iso-Propylthioprop-2-yl 16 H 2-tert.-Butylthioprop-2-yl 17 H Methyl 18 H Ethyl 19 H n-Propyl 20 H iso-Propyl 21 H n-Butyl 22 H iso-Butyl 23 H sec.-Butyl 24 H tert.-Butyl 25 H n-Hexyl 26 H n-Decyl 27 H Cyclopropyl 28 H Cyclohexyl 29 H Phenylthiomethyl 30 H 2-Phenylthiomethyl 31 H 2-(2′-Chlorophenylthio)prop-2-yl 32 H Ethynyl 33 H 1-Propynyl 34 H Methoxy 35 H Ethoxy 36 H n-Propoxy 37 H iso-Propoxy 38 H n-Butoxy 39 H iso-Butoxy 40 H sec.-Butoxy 41 H tert.-Butoxy 42 H Methylthio 43 H Ethylthio 44 H n-Propylthio 45 H iso-Propylthio 46 H n-Butylthio 47 H iso-Butyl 48 H sec.-Butyl 49 H tert.-Butyl 50 H Benzylthio 51 H Trifluoromethoxy 52 H Cyano 53 H Amin 54 H Methylamino 55 H Dimethylamino 56 H Ethylamino 57 H Diethylamino 58 H Di-n-Propylamino 59 H Di-iso-Propylamino 60 H Di-n-Butylamino 61 H Di-iso-Butylamino 62 H Acetyl 63 H Propion-1-yl 64 H Butyr-1-yl 65 H iso-Butyr-1-yl 66 H Pivaloyl 67 H Benzoyl 68 H 4-Chlorobenzoyl 69 H Benzylcarbonyl 70 H Methoxycarbonyl 71 H Ethoxycarbonyl 72 H n-Propoxycarbonyl 73 H iso-Propoxycarbonyl 74 H n-Butoxycarbonyl 75 H iso-Butoxycarbonyl 76 H sec.-Butoxycarbonyl 77 H tert.-Butoxycarbonyl 78 H n-Hexoxycarbonyl 79 H Phenoxycarbonyl 80 H 4-Chlorophenoxycarbonyl 81 H Benzyloxycarbonyl 82 H Aminocarbonyl 83 H Dimethylaminocarbonyl 84 H Diethylaminocarbonyl 85 H Di-iso-Propylaminocarbonyl 86 H Phenylaminocarbonyl 87 H N-Methyl-N-Phenylamino- carbonyl 88 H Phenyl 89 H 2-Fluorophenyl m.p.: 69-71° C. 90 H 3-Fluorophenyl m.p.: 74-77° C. 91 H 4-Fluorophenyl m.p.: 73-76° C. IR (KBr): 1699, 1278, 1271, 1256, 1225 92 H Pentafluorophenyl m.p.: 94-96° C.; IR (KBr): 1704, 1527, 1494, 1133 93 H 2-Chlorophenyl ¹H-NMR (CDCl₃): δ = 3.70s, 3.82s, 5.15s, 7.15- 7.40m, 7.52m, 7.60s, 7.85m, 8.52s 94 H 3-Chlorophenyl m.p.: 48-50° C.; 95 H 4-Chlorophenyl (v. Example 6) 96 H Pentachlorophenyl 97 H 2,3-Dichlorophenyl m.p.: 103-105° C.; 98 H 2,4-Dichlorophenyl m.p.: 94-96° C.; 99 H 2,5-Dichlorophenyl 100 H 2,6-Dichlorophenyl m.p.: 118-120° C.; 101 H 3,4-Dichlorophenyl m.p.: 82-84° C.; 102 H 3,5-Dichlorophenyl m.p.: 94-96° C.; 103 H 2,3,4-Trichlorophenyl 104 H 2,3,5-Trichlorophenyl 105 H 2,3,6-Trichlorophenyl 106 H 2,4,5-Trichlorophenyl 107 H 2,3,6-Trichlorophenyl 108 H 3,4,5-Trichlorophenyl 109 H 2,3,4,6-Tetrachlorophenyl 110 H 2,3,5,6-Tetrachlorophenyl 111 H 2-Bromophenyl m.p.: 85-87° C.; 112 H 3-Bromophenyl ¹H-NMR (CDCl₃): δ = 3.68s, 3.79s, 5.13, 7.15-7.54 m, 7.59s 7.74s, 8.00s 113 H 4-Bromophenyl m.p.: 131-134° C.; 114 H 2,4-Dibromophenyl 115 H 3-Brom-4-fluorophenyl 116 H 3-Brom-4-methoxyphenyl 117 H 2-Iodophenyl 118 H 3-Iodophenyl 119 H 4-Iodophenyl 120 H 2-Chloro-4-fluorophenyl m.p.: 112-115° C.; 121 H 2-Chloro-5-fluorophenyl 122 H 2-Chloro-6-fluorophenyl m.p.: 80-82° C.; 123 H 2-Chloro-4-bromophenyl 124 H 2-Bromo-4-chlorophenyl 125 H 2-Bromo-4-bromophenyl 126 H 3-Bromo-4-chlorophenyl 127 H 3-Chloro-4-fluorophenyl 128 H 3-Fluoro-4-chlorophenyl 129 H 2-Cyanophenyl 130 H 3-Cyanophenyl 131 H 4-Cyanophenyl 132 H 2-Nitrophenyl 133 H 3-Nitrophenyl 134 H 4-Nitrophenyl m.p.: 147-155° C.; 135 H 2-Methylphenyl m.p.: 57-59° C.; 136 H 3-Methylphenyl m.p.: 54-56° C.; 137 H 4-Methylphenyl m.p.: 86-88° C.; 138 H 2,4-Dimethylphenyl m.p.: 75-77° C.; 139 H 2,6-Dimethylphenyl 140 H 3,4-Dimethylphenyl 141 H 3,5-Dimethylphenyl 142 H 2,3,4-Trimethylphenyl 143 H 2,3,5-Trimethylphenyl 144 H 2,3,6-Trimethylphenyl 145 H 2,4,5-Trimethylphenyl 146 H 2,4,6-Trimethylphenyl 147 H 3,4,5-Trimethylphenyl 148 H Pentamethylphenyl 149 H 2-Ethylphenyl 150 H 3-Ethylphenyl 151 H 4-Ethylphenyl 152 H 3,5-Diethylphenyl 153 H 2-n-Propylphenyl 154 H 3-n-Propylphenyl 155 H 4-n-Propylphenyl 156 H 2-iso-Propylphenyl 157 H 3-iso-Propylphenyl 158 H 4-iso-Propylphenyl 159 H 2,4-Di-iso-Propylphenyl 160 H 3,5-Di-iso-Propylphenyl 161 H 4-n-Butylphenyl 162 H 4-sec.-Butylphenyl 163 H 4-iso-Butylphenyl 164 H 4-tert.-Butylphenyl m.p.: 71-73° C. 165 H 3-tert.-Butylphenyl 166 H 2-tert.-Butylphenyl 167 H 2,4-Di-tert.-Butylphenyl 168 H 3,5-Di-tert.-Butylphenyl 169 H 4-n-Hexylphenyl 170 H 4-n-Dodecylphenyl 171 H 2-Methyl-4-tert.-Butylphenyl 172 H 2-Methyl-6-tert.-Butylphenyl 173 H 2-Methyl-4-iso-Butylphenyl 174 H 2-Methyl-4-cyclohexylphenyl 175 H 2-Methyl-4-phenylphenyl 176 H 2-Methyl-4-benzylphenyl 177 H 2-Methyl-4-phenoxyphenyl 178 H 2-Methyl-4-benzyloxyphenyl 179 H 2-Methyl-3-chlorophenyl 180 H 2-Methyl-4-chlorophenyl 181 H 2-Methyl-5-chlorophenyl 182 H 2-Methyl-6-chlorophenyl 183 H 2-Methyl-4-fluorophenyl 184 H 2-Methyl-3-bromophenyl 185 H 2-Methyl-4-bromophenyl 186 H 2-Methyl-3-methoxyphenyl 187 H 2-Methyl-4-methoxyphenyl 188 H 2-Methyl-5-methoxyphenyl 189 H 2-Methyl-6-methoxyphenyl 190 H 2-Methyl-4-iso-Propoxyphenyl 191 H 2-Methyl-2,5-dimethoxyphenyl 192 H 2-Methoxyphenyl m.p.: 52-54° C. 193 H 3-Methoxyphenyl ¹H-NMR (CDCl₃): δ = 3.65s, 3.76s, 3.80s, 5.12s, 6.88-7.54m, 7.58s 8.05s 194 H 4-Methoxyphenyl m.p.: 61-63° C. 195 H 2,3-Dimethoxyphenyl 196 H 2,4-Dimethoxyphenyl m.p.: 70-72° C. 197 H 2,5-Dimethoxyphenyl 198 H 2,6-Dimethoxyphenyl 199 H 3,4-Dimethoxyphenyl 200 H 3,5-Dimethoxyphenyl m.p.: 79-82° C. 201 H 3,6-Dimethoxyphenyl 202 H 2,3,4-Trimethoxyphenyl 203 H 2,3,5-Trimethoxyphenyl 204 H 2,3,6-Trimethoxyphenyl 205 H 2,4,5-Trimethoxyphenyl 206 H 2,3,6-Trimethoxyphenyl 207 H 3,4,5-Trimethoxyphenyl 208 H 2-Ethoxyphenyl 209 H 3-Ethoxyphenyl ¹H-NMR (CDCl₃): δ = 1.39t, 3.67s, 3.80s, 4.02q, 5.12s, 6.87- 7.54m, 7.58s, 8.05s 210 H 4-Ethoxyphenyl m.p.: 93-94° C. 211 H 2-iso-Propoxyphenyl 212 H 3-iso-Propoxyphenyl 213 H 4-iso-Propoxyphenyl 214 H 3-tert.-Butoxyphenyl 215 H 4-tert.-Butoxyphenyl ¹H-NMR (CDCl₃): δ = 1.36s, 3.68s, 3.78s, 5.09s, 6.94-7.53m, 7.58s, 8.07s 216 H 2-Trifluoromethoxyphenyl 217 H 3-Trifluoromethoxyphenyl 218 H 4-Trifluoromethoxyphenyl 219 H 3-(1′,1′,2′,2′- Tetrafluoro)ethoxyphenyl 220 H 4-(1′,1′,2′,2′- Tetrafluoro)ethoxyphenyl 221 H 2-Chloromethylphenyl 222 H 3-Chloromethylphenyl 223 H 4-Chloromethylphenyl 224 H 2-Trifluoromethylphenyl m.p.: 75-77° C. 225 H 3-Trifluoromethylphenyl 226 H 4-Trifluoromethylphenyl m.p.: 111-114° C. 227 H 2-(Methoxyiminomethyl)phenyl 228 H 3-(Methoxyiminomethyl)phenyl 229 H 4-(Methoxyiminomethyl)phenyl 230 H 2-(Ethoxyiminomethyl)phenyl 231 H 3-(Ethoxyiminomethyl)phenyl 232 H 4-(Ethoxyiminomethyl)phenyl 233 H 2-(n-Propoxyiminomethyl)phenyl 234 H 3-(n-Propoxyiminomethyl)phenyl 235 H 4-(n-Propoxyiminomethyl)phenyl 236 H 2-(iso-Propoxyiminomethyl)- phenyl 237 H 3-(iso-Propoxyiminomethyl)- phenyl 238 H 4-(iso-Propoxyiminomethyl)- phenyl 239 H 2-(n-Butoxyiminomethyl)phenyl 240 H 3-(n-Butoxyiminomethyl)phenyl 241 H 4-(n-Butoxyiminomethyl)phenyl 242 H 2-(iso-Butoxyiminomethyl)phenyl 243 H 3-(iso-Butoxyiminomethyl)phenyl 244 H 4-(iso-Butoxyiminomethyl)phenyl 245 H 2-(tert.-Butoxyiminomethyl)- phenyl 246 H 3-(tert.-Butoxyiminomethyl)- phenyl 247 H 4-(tert.-Butoxyiminomethyl)- phenyl 248 H 2-(n-Pentoxyiminomethyl)phenyl 249 H 3-(n-Pentoxyiminomethyl)phenyl 250 H 4-(n-Pentoxyiminomethyl)phenyl 251 H 2-(n-Hexoxyiminomethyl)phenyl 252 H 3-(n-Hexoxyiminomethyl)phenyl 253 H 4-(n-Hexoxyiminomethyl)phenyl 254 H 2-(Allyloxyiminomethyl)phenyl 255 H 3-(Allyloxyiminomethyl)phenyl 256 H 4-(Allyloxyiminomethyl)phenyl 257 H 2-(Benzyloxyiminomethyl)phenyl 258 H 3-(Benzyloxyiminomethyl)phenyl 259 H 4-(Benzyloxyiminomethyl)phenyl 260 H 2-(Methoxyimino-1′-ethyl)phenyl 261 H 3-(Methoxyimino-1′-ethyl)phenyl 262 H 4-(Methoxyimino-1′-ethyl)phenyl 263 H 2-(Ethoxyimino-1′-ethyl)phenyl 264 H 3-(Ethoxyimino-1′-ethyl)phenyl 265 H 4-(Ethoxyimino-1′-ethyl)phenyl 266 H 2-(n-Propoxyimino-1′-ethyl)- phenyl 267 H 3-(n-Propoxyimino-1′-ethyl)- phenyl 268 H 4-(n-Propoxyimino-1′-ethyl)- phenyl 269 H 2-(n-Butoxyamino-1′-ethyl)phenyl 270 H 3-(n-Butoxyamino-1′-ethyl)phenyl 271 H 4-(n-Butoxyamino-1′-ethyl)phenyl 272 H 2-(n-Pentoxyimino-1′-ethyl)- phenyl 273 H 3-(n-Pentoxyimino-1′-ethyl)- phenyl 274 H 4-(n-Pentoxyimino-1′-ethyl)- phenyl 275 H 2-(n-Hexoxyimino-1′-ethyl)phenyl 276 H 3-(n-Hexoxyimino-1′-ethyl)phenyl 277 H 4-(n-Hexoxyimino-1′-ethyl)phenyl 278 H 2-(Allyloxyimino-1′-ethyl)phenyl 279 H 3-(Allyloxyimino-1′-ethyl)phenyl 280 H 4-(Allyloxyimino-1′-ethyl)phenyl 281 H 2-(Benzyloxyimino-1′-ethyl)- phenyl 282 H 3-(Benzyloxyimino-1′-ethyl)- phenyl 283 H 4-(Benzyloxyimino-1′-ethyl)- phenyl 284 H 2-Phenylphenyl 285 H 3-Phenylphenyl 286 H 4-Phenylphenyl m.p.: 94-96° C. 287 H 2-Phenoxyphenyl 288 H 3-Phenoxyphenyl 289 H 4-Phenoxyphenyl 290 H 2-Benzyloxyphenyl 291 H 3-Benzyloxyphenyl 292 H 4-Benzyloxyphenyl m.p.: 94-96° C. 293 H 4-(Imidazol-1′-yl)phenyl 294 H 4-(Piperazin-1′-yl)phenyl 295 H 4-(Morpholin-1′-yl)phenyl 296 H 4-(Piperazin-1′-yl)phenyl 297 H 4-(Pyridyl-2′-oxy)phenyl 298 H 2-Cyclopropylphenyl 299 H 3-Cyclopropylphenyl 300 H 4-Cyclopropylphenyl 301 H 3-Cyclohexylphenyl 302 H 4-Cyclohexylphenyl 303 H 4-Oxiramylphenyl 304 H 4-(1′,3′-Dioxo-2′-yl)phenyl 305 H 4-(Tetrahydropyran-2-yloxy)- phenyl 306 H 1-Naphthyl 307 H 2-Naphthyl oil: IR (film): 1707, 1633, 1257, 1129, 110 308 H 9-Anthryl 309 H 1-Naphthoxy 310 H 2-Naphthoxy 311 H 9-Anthroxy 312 H Phenoxy 313 H 2-Chlorophenoxy 314 H 3-Chlorophenoxy 315 H 4-Chlorophenoxy 316 H 4-Methylphenoxy 317 H 4-tert.-Butylphenoxy 318 H 4-Methylphenoxy 319 H 4-Ethoxyphenoxy 320 H 4-tert.-Butoxyphenoxy 321 H Phenylthio 322 H 2-Chlorophenylthio 323 H 4-Chlorophenylthio 324 H Benzyl 325 H 2-Methylbenzyl 326 H 3-Methylbenzyl 327 H 4-Methylbenzyl 328 H 4-tert.-Butylbenzyl 329 H 2-Chlorobenzyl 330 H 3-Chlorobenzyl 331 H 4-Chlorobenzyl 332 H 2,4-Dichlorobenzyl 333 H 2,6-Dichlorobenzyl 334 H 2,4,6-Trichlorobenzyl 335 H 2-Trifluoromethylbenzyl 336 H 3-Trifluoromethylbenzyl 337 H 4-Trifluoromethylbenzyl 338 H 2-Methoxybenzyl 339 H 4-Methoxybenzyl 340 H 4-tert.-Butoxybenzyl 341 H 4-Phenoxybenzyl 342 H 1-Phenethyl 343 H 2-Phenethyl 344 H 1-Phenylpropyl 345 H 2-Phenylpropyl 346 H 3-Phenylpropyl 347 H 2-Methyl-2-phenylpropyl 348 H 2-Methyl-3-phenylpropyl 349 H 4-Phenylbutyl 350 H 2-Phenyl-1-ethenyl 351 H 1-Phenyl-1-ethenyl 352 H 1-Phenyl-1-propenyl 353 H 1-Phenyl-1-propen-2-yl 354 H 2,2-Diphenylethenyl 355 H Phenoxymethyl 356 H 2-Pyridyl 357 H 3-Pyridyl 358 H 4-Pyridyl 359 H 2,6-Pyrimidinyl 360 H 1,5-Pyrimidinyl 361 H 2-Thienyl 362 H 3-Thienyl 363 H 2-Furyl 364 H 3-Furyl 365 H 1-Pyrrolyl 366 H 1-Imidazolyl 367 H 1,2,4-Triazolyl 368 H 1,3,4-Triazolyl 369 H 4-Thiazolyl 370 H 2-Benzothiazolyl 371 H 2-Pyridyloxy 372 H 2-Pyrimidinyloxy 373 H 2-Pyridylthio 374 H 2-Pyrimidinylthio 375 H 2-Benzothiazolylthio 376 H Phenylthiomethyl 377 H 2-Pyridylmethyl 378 H 3-Pyridylmethyl 379 H Furfuryloxy 380 H Thienylmethoxy 381 H 3-Isoxazolylmethoxy 382 H 2-Oxazolylmethoxy 383 H 2-Pyridylmethoxy 384 H 2′-Furyl-2-ethenyl 385 H 2′-Thienyl-2-thenyl 386 H 3′-Pyridyl-2-ethenyl 387 H Oxiranyl 388 H 1-Azinidiayl 389 H 1-Azetidinyl 390 H 1-Pyrrolidinyl 391 H 2-Tetrahydrofuryl 392 H 2-Tetrahydropyranyl 393 H 3-Tetrahydropyranyl 394 H 1-Piperidinyl 395 H 1-Morpholinyl 396 H 1-Piperazinyl 397 H 1,3-Dioxan-2-yl 398 H 3-Tetrahydrothiopyranyl 399 H 2-Dihydropyranyloxy 400 H 2-Tetrahydropyranyloxy 401 H CF₃ 402 H 2-Fluoroethyl 403 H 2,2,2-Trifluoroethyl 404 H Pentafluoroethyl 405 H Chloromethyl 406 H Dichloromethyl 407 H Trichloromethyl 408 H 2-Chloroethyl 409 H 2,2,2-Trichloroethyl 410 H Pentachoroethyl 411 H Cyclopropyl 412 H Cycloburyl 413 H Cyclopentyl 414 H Cyclohexyl 415 H 1-Methylcyclopropyl 416 H 2,2-Dimethylcyclopropyl 417 H 1-Methylcyclohexyl 418 H 2,2-Difluorocyclopropyl 419 H 2,2-Dichlorocyclopropyl 420 H 2,2-Dibromocyclopropyl 421 H 2,2-Dichloro-3-Methylcyclo- propyl 422 H 2,2,3,3-Tetrafluorocyclobutyl 423 H Ethenyl 424 H 1-Propenyl 425 H 2-Methyl-1-propenyl 426 H 4-Methylpem-3-en-1-yl 427 H 2-Propenyl 428 H 2-Butenyl 429 H 2-Methyl-1-propenyl 430 H 3-Methyl-2-butenyl 431 H 2,2-Difluoroethenyl 432 H 2,2-Dichloroethenyl 433 H 3,3,3-Trifluoropropenyl 434 H 3,3,3-Trichloropropenyl 435 H 3-Chloro-2-propenyl 436 H Cyclopent-1-enyl 437 H Cyclopentadienyl 438 H Cyclohex-1-enyl 439 H Pentafluorocyclopentadienyl 440 H Pentachlorocyclopentadienyl 441 H 4-Dimethylaminophenyl m.p.: 90-92° C. 442 H 4-n-Butoxyphenyl m.p.: 79-82° C.

TABLE VI

No. R³ R⁴ Data 1 H H m.p.: 94-95° C. 2 H Methoxymethyl 3 H Ethoxymethyl 4 H n-Propoxymethyl 5 H iso-Propoxymethyl 6 H tert.-Butoxymethyl 7 H 2-Methoxyprop-2-yl 8 H 2-Ethoxyprop-2-yl 9 H 2-n-Propoxyprop-2-yl 10 H 2-iso-Propoxyprop-2-yl 11 H 2-tert.-Butoxyprop-2-yl 12 H Methylthiomethyl 13 H tert.-Butylthiomethyl 14 H 2-Methylthioprop-2-yl 15 H 2-iso-Propylthioprop-2-yl 16 H 2-tert.-Butylthioprop-2-yl 17 H Methyl 18 H Ethyl 19 H n-Propyl 20 H iso-Propyl 21 H n-Butyl 22 H iso-Butyl 23 H sec.-Butyl 24 H tert.-Butyl 25 H n-Hexyl 26 H n-Decyl 27 H Cyclopropyl 28 H Cyclohexyl 29 H Phenylthiomethyl 30 H 2-Phenylthiomethyl 31 H 2-(2′-Chlorophenylthio)prop-2-yl 32 H Ethynyl 33 H I-Propynyl 34 H Methoxy 35 H Ethoxy 36 H n-Propoxy 37 H iso-propoxy 38 H n-Butoxy 39 H iso-Butoxy 40 H sec.-Butoxy 41 H tert.-Butoxy 42 H Methylthio 43 H Ethylthio 44 H n-Propylthio 45 H iso-Propylthio 46 H n-Butylthio 47 H iso-Butylthio 48 H sec.-Butylthio 49 H tert.-Butylthio 50 H Benzylthio 51 H Trifluoromethoxy 52 H Cyano 53 H Amino 54 H Methylamino 55 H Dimethylamino 56 H Ethylamino 57 H Diethylamino 58 H Di-n-Propylamino 59 H Di-iso-Propylamino 60 H Di-n-Butylamino 61 H Di-iso-Butylamino 62 H Acetyl 63 H Propion-1-yl 64 H Butyr-1-yl 65 H iso-Butyr-1-yl 66 H Pivaloyl 67 H Benzoyl 68 H 4-Chlorobenzoyl 69 H Benzylcarbonyl 70 H Methoxycarbonyl 71 H Ethoxycarbonyl 72 H n-Propoxycarbonyl 73 H iso-Propoxycarbonyl 74 H n-Butoxycarbonyl 75 H iso-Butoxycarbonyl 76 H sec.-Butoxycarbonyl 77 H tert.-Butoxycarbonyl 78 H n-Hexoxycarbonyl 79 H Phenoxycarbonyl 80 H 4-Chlorophenoxycarbonyl 81 H Benzyloxycarbonyl 82 H Aminocarbonyl 83 H Dimethylaminocarbonyl 84 H Diethylaminocarbonyl 85 H Di-iso-Propylaminocarbonyl 86 H Phenylaminocarbonyl 87 H N-Methyl-N-Phenylamino- carbonyl 88 H Phenyl m.p.: 92-95° C. 89 H 2-Fluorophenyl m.p.: 92-95° C. 90 H 3-Fluorophenyl m.p.: 58-60° C. 91 H 4-Fluorophenyl m.p.: 110-111° C. 92 H Pentafluorophenyl m.p.: 118-120° C. 93 H 2-Chlorophenyl ¹H—NMR (CDCl₃): δ = 3.70s, 3.82s, 5.15s, 7.15- 7.40m, 7.52m, 7.60s, 7.85m, 8.52s 94 H 3-Chlorophenyl m.p.: 58-60° C. 95 H 4-Chlorophenyl m.p.: 146-148° C. 96 H Pentachlorophenyl 97 H 2,3-Dichlorophenyl m.p.: 95-97° C. 98 H 2,4-Dichlorophenyl m.p.: 58-62° C. 99 H 2,5-Dichlorophenyl 100 H 2,6-Dichlorophenyl m.p.: 136-140° C. 101 H 3,4-Dichlorophenyl m.p.: 94-97° C. 102 H 3,5-Dichlorophenyl m.p.: 88-91° C. 103 H 2,3,4-Trichlorophenyl 104 H 2,3,5-Trichlorophenyl 105 H 2,3,6-Trichlorophenyl 106 H 2,4,5-Trichlorophenyl 107 H 2,4,6-Trichlorophenyl 108 H 3,4,5-Trichlorophenyl 109 H 2,3,4,6-Tetrachlorophenyl 110 H 2,3,5,6-Tetrachlorophenyl 111 H 2-Bromophenyl m.p.: 91-94° C. 112 H 3-Bromophenyl m.p.: 63-64° C. 113 H 4-Bromophenyl m.p.: 145-147° C. 114 H 2,4-Dibromophenyl 115 H 3-Bromo-4-Fluorophenyl 116 H 3-Bromo-4-Methoxyphenyl 117 H 2-Iodophenyl 118 H 3-Iodophenyl 119 H 4-Iodophenyl 120 H 2-Chloro-4-Fluorophenyl m.p.: 90-93° C. 121 H 2-Chloro-5-Fluorophenyl 122 H 2-Chloro-6-Fluorophenyl m.p.: 111-113° C. 123 H 2-Chloro-4-Bromophenyl 124 H 2-Bromo-4-Chlorophenyl 125 H 2-Bromo-4-Fluorophenyl 126 H 3-Bromo-4-Chlorophenyl 127 H 3-Chloro-4-Fluorophenyl 128 H 3-Fluoro-4-Chlorophenyl 129 H 2-Cyanophenyl 130 H 3-Cyanophenyl 131 H 4-Cyanophenyl 132 H 2-Nitrophenyl 133 H 3-Nitrophenyl 134 H 4-Nitrophenyl m.p.: 142-146° C. 135 H 2-Methylphenyl m.p.: 58-60° C. 136 H 3-Methylphenyl m.p.: 70-72° C. 137 H 4-Methylphenyl m.p.: 99-102° C. 138 H 2,4-Dimethylphenyl m.p.: 54-56° C. 139 H 2,6-Dimethylphenyl 140 H 3,4-Dimethylphenyl 141 H 3,5-Dimethylphenyl 142 H 2,3,4-Trimethylphenyl 143 H 2,3,5-Trimethylphenyl 144 H 2,3,6-Trimethylphenyl 145 H 2,4,5-Trimethylphenyl 146 H 2,4,6-Trimethylphenyl 147 H 3,4,5-Trimethylphenyl 148 H Pentamethylphenyl 149 H 2-Ethylphenyl 150 H 3-Ethylphenyl 151 H 4-Ethylphenyl 152 H 3,5-Diethylphenyl 153 H 2-n-Propylphenyl 154 H 3-n-Propylphenyl 155 H 4-n-Propylphenyl 156 H 2-iso-Propylphenyl 157 H 3-iso-Propylphenyl 158 H 4-iso-Propylphenyl 159 H 2,4-Di-iso-Propylphenyl 160 H 3,5-Di-iso-Propylphenyl 161 H 4-n-Butylphenyl 162 H 4-sec.-Butylphenyl 163 H 4-iso-Butylphenyl 164 H 4-tert.-Butylphenyl m.p.: 82-84° C. 165 H 3-tert.-Butylphenyl 166 H 2-tert.-Butylphenyl 167 H 2,4-Di-tert.-Butylphenyl 168 H 3,5-Di-tert.-Butylphenyl 169 H 4-n-Hexylphenyl 170 H 4-n-Dodecylphenyl 171 H 2-Methyl-4-tert.-Butylphenyl 172 H 2-Methyl-6-tert.-Butylphenyl 173 H 2-Methyl-4-iso-Propylphenyl 174 H 2-Methyl-4-Cyclohexylphenyl 175 H 2-Methyl-4-Phenylphenyl 176 H 2-Methyl-4-Benzylphenyl 177 H 2-Methyl-4-Phenoxyphenyl 178 H 2-Methyl-4-Benzyloxyphenyl 179 H 2-Methyl-3-Chlorophenyl 180 H 2-Methyl-4-Chlorophenyl 181 H 2-Methyl-5-Chlorophenyl 182 H 2-Methyl-6-Chlorophenyl 183 H 2-Methyl-4-Fluorophenyl 184 H 2-Methyl-3-Bromophenyl 185 H 2-Methyl-4-Bromophenyl 186 H 2-Methyl-3-Methoxyphenyl 187 H 2-Methyl-4-Methoxyphenyl 188 H 2-Methyl-5-Methoxyphenyl 189 H 2-Methyl-6-Methoxyphenyl 190 H 2-Methyl-4-iso-Propoxyphenyl 191 H 2-Methyl-2,5-Dimethoxyphenyl 192 H 2-Methoxyphenyl m.p.: 65-68° C. 193 H 3-Methoxyphenyl m.p.: 83-84° C. 194 H 4-Methoxyphenyl m.p.: 88-90° C. 195 H 2,3-Dimethoxyphenyl 196 H 2,4-Dimethoxyphenyl m.p.: 90-93° C. 197 H 2,5-Dimethoxyphenyl 198 H 2,6-Dimethoxyphenyl 199 H 3,4-Dimethoxyphenyl m.p.: 70-72° C. 200 H 3,5-Dimethoxyphenyl m.p.: 92-99° C. 201 H 3,6-Dimethoxyphenyl 202 H 2,3,4-Trimethoxyphenyl 203 H 2,3,5-Trimethoxyphenyl 204 H 2,3,6-Trimethoxyphenyl 205 H 2,4,5-Trimethoxyphenyl 206 H 2,4,6-Trimethoxyphenyl 207 H 3,4,5-Trimethoxyphenyl m.p.: 105-109° C. 208 H 2-Ethoxyphenyl 209 H 3-Ethoxyphenyl m.p.: 90-92° C. 210 H 4-Ethoxyphenyl m.p.: 97-98° C. 211 H 2-iso-Propoxyphenyl 212 H 3-iso-Propoxyphenyl 213 H 4-iso-Propoxyphenyl 214 H 3-tert.-Butoxyphenyl 215 H 4-tert.-Butoxyphenyl m.p.: 78-83° C. 216 H 2-Trifluoromethoxyphenyl 217 H 3-Trifluoromethoxyphenyl 218 H 4-Trifluoromethoxyphenyl 219 H 3-(1′,1′,2′,2′- Tetrafluoro)ethoxyphenyl 220 H 4-(1′,1′,2′,2′- Tetrafluoro)ethoxyphenyl 221 H 2-Chloromethylphenyl 222 H 3-Chloromethylphenyl 223 H 4-Chloromethylphenyl 224 H 2-Trifluoromethylphenyl m.p.: 58-60° C. 225 H 3-Trifluoromethylphenyl m.p.: 74-77° C. 226 H 4-Trifluoromethylphenyl m.p.: 120-122° C. 227 H 2-(Methoxyiminomethyl)phenyl 228 H 3-(Methoxyiminomethyl)phenyl 229 H 4-(Methoxyiminomethyl)phenyl 230 H 2-(Ethoxyiminomethyl)phenyl 231 H 3-(Ethoxyiminomethyl)phenyl 232 H 4-(Ethoxyiminomethyl)phenyl 233 H 2-(n-Propoxyiminomethyl)phenyl 234 H 3-(n-Propoxyiminomethyl)phenyl 235 H 4-(n-Propoxyiminomethyl)phenyl 236 H 2-(iso-Propoxyiminomethy)- phenyl 237 H 3-(iso-Propoxyiminomethyl)- phenyl 238 H 4-(iso-Porpoxyiminomethyl)- phenyl 239 H 2-(n-Butoxyiminomethyl)phenyl 240 H 3-(n-Butoxyiminomethyl)phenyl 241 H 4-(n-Butoxyiminomethyl)phenyl 242 H 2-(iso-Butoxyiminomethyl)phenyl 243 H 3-(iso-Butoxyiminomethyl)phenyl 244 H 4-(iso-Butoxyiminomethyl)phenyl 245 H 2-(tert.-Butoxyiminomethyl)- phenyl 246 H 3-(tert.-Butoxyiminomethyl)- phenyl 247 H 4-(tert.-Butoxyiminomethyl)- phenyl 248 H 2-(n-Pentoxyiminomethyl)phenyl 249 H 3-(n-Pentoxyiminomethyl)phenyl 250 H 4-(n-Pentoxyiminomethyl)phenyl 251 H 2-(n-Hexoxyiminomethyl)phenyl 252 H 3-(n-Hexoxyiminomethyl)phenyl 253 H 4-(n-Hexoxyiminomethyl)phenyl 254 H 2-(Allyloxyiminomethyl)phenyl 255 H 3-(Allyloxyiminomethyl)phenyl 256 H 4-(Allyloxyiminomethyl)phenyl 257 H 2-(Benzyloxyiminomethyl)phenyl 258 H 3-(Benzyloxyiminomethyl)phenyl 259 H 4-(Benzyloxyiminomethyl)phenyl 260 H 2-(Methoxyimino-1′-ethyl)phenyl 261 H 3-(Methoxyimino-1′-ethyl)phenyl 262 H 4-(Methoxyimino-1′-ethyl)phenyl 263 H 2-(Ethoxyimino-1′-ethyl)phenyl 264 H 3-(Ethoxyimino-1′-ethyl)phenyl 265 H 4-(Ethoxyimino-1′-ethyl)phenyl 266 H 2-(n-Propoxyimino-1′-ethyl)- phenyl 267 H 3-(n-Propoxyimino-1′-ethyl)- phenyl 268 H 4-(n-Propoxyimino-1′-ethyl)- phenyl 269 H 2-(n-Butoxyamino-1′-ethyl)phenyl 270 H 3-(n-Butoxyamino-1′-ethyl)phenyl 271 H 4-(n-Butoxyamino-1′-ethyl)phenyl 272 H 2-(n-Pentoxyimino-1′-ethyl)- phenyl 273 H 3-(n-Pentoxyimino-1′-ethyl)- phenyl 274 H 4-(n-Pentoxyimino-1′-ethyl)- phenyl 275 H 2-(n-Hexoxyimino-1′-ethyl)phenyl 276 H 3-(n-Hexoxyimino-1′-ethyl)phenyl 277 H 4-(n-Hexoxyimino-1′-ethyl)phenyl 278 H 2-(Allyloxyimino-1′-ethyl)phenyl 279 H 3-(Allyloxyimino-1′-ethyl)phenyl 280 H 4-(Allyloxyimino-1′-ethyl)phenyl 281 H 2-(Benzyloxyimino-′-ethyl)- phenyl 282 H 3-(Benzyloxyimino-1′-ethyl)- phenyl 283 H 4-(Benzyloxyimino-1′-ethyl)- phenyl 284 H 2-Phenylphenyl 285 H 3-Phenylphenyl 286 H 4-Phenylphenyl m.p.: 100-102° C. 287 H 2-Phenoxyphenyl 288 H 3-Phenoxyphenyl IR (film): 1728, 1489, 1247, 1214, 1070, 1020 289 H 4-Phenoxyphenyl m.p.: 85-87° C. 290 H 2-Benzyloxyphenyl m.p.: 83-85° C. 291 H 3-Benzyloxyphenyl m.p.: 66-68° C. 292 H 4-Benzyloxyphenyl m.p.: 104-106° C. 293 H 4-(Imidazol-1′-yl)phenyl 294 H 4-(Piperazin-1′-yl)phenyl 295 H 4-(Morpholin-1′-yl)phenyl 296 H 4-(Piperazin-1′-yl)phenyl 297 H 4-(Pyridyl-2′-oxy)phenyl 298 H 2-Cyclopropylphenyl 299 H 3-Cyclopropylphenyl 300 H 4-Cyclopropylphenyl 301 H 3-Cyclohexylphenyl 302 H 4-Cyclohexylphenyl 303 H 4-Oxiranylphenyl 304 H 4-(1′,3′-Dioxan-2′-yl)phenyl 305 H 4-(Tetrahydropyran-2-yloxy)- phenyl 306 H 1-Naphthyl m.p.: 70-73° C. 307 H 2-Naphyhyl m.p.: 125-126° C. 308 H 9-Anthryl 309 H 1-Naphthoxy 310 H 2-Naphthoxy 311 H 9-Anthroxy 312 H Phenoxy 313 H 2-Chlorophenoxy 314 H 3-Chlorophenoxy 315 H 4-Chlorophenoxy 316 H 4-Methylphenoxy 317 H 4-tert.-Butylphenoxy 318 H 4-Methoxyphenoxy 319 H 4-Ethoxyphenoxy 320 H 4-tert.-Butoxyphenoxy 321 H Phenylthio 322 H 2-Chlorophenylthio 323 H 4-Chlorophenylthio 324 H Benzyl 325 H 2-Methylbenzyl 326 H 3-Methylbenzyl 327 H 4-Methylbenzyl 328 H 4-tert.-Butylbenzyl 329 H 2-Chlorobenzyl 330 H 3-Chlorobenzyl 331 H 4-Chlorobenzyl 332 H 2,4-Dichlorobenzyl 333 H 2,6-Dichlorobenzyl 334 H 2,4,6-Trichlorobenzyl 335 H 2-Trifluoromethylbenzyl 336 H 3-Trifluoromethylbenzyl 337 H 4-Trifluoromethylbenzyl 338 H 2-Methoxybenzyl 339 H 4-Methoxybenzyl 340 H 4-tert.-Butoxybenzyl 341 H 4-Phenoxybenzyl 342 H 1-Phenethyl 343 H 2-Phenethyl 344 H 1-Phenylpropyl 345 H 2-Phenylpropyl 346 H 3-Phenylpropyl 347 H 2-Methyl-2-phenylpropyl 348 H 2-Methyl-3-phenylpropyl 349 H 4-Phenylbutyl 350 H 2-Phenyl-1-ethenyl 351 H 1-Phenyl-1-ethenyl 352 H 1-Phenyl-1-propenyl 353 H 1-Phenyl-1-porpen-2-yl 354 H 2,2-Diphenylethenyl 355 H Phenoxymethyl 356 H 2-Pyridyl 357 H 3-Pyridyl 358 H 4-Pyridyl 359 H 2,6-Pyrimidinyl 360 H 1,5-Pyrimidinyl 361 H 2-Thienyl 362 H 3-Thienyl 363 H 2-Furyl 364 H 3-Furyl 365 H 1-Pyrrolyl 366 H 1-Imidazolyl 367 H 1,2,4-Triamolyl 368 H 1,3,4-Triamolyl 369 H 4-Thiazolyl 370 H 2-Benzothiazolyl 371 H 2-Pyridyloxy 372 H 2-Pyrimidinyloxy 373 H 2-Pyridylthio 374 H 2-Pyrimidinylthio 375 H 2-Benzothimzolylthio 376 H Phenylthiomethyl 377 H 2-Pyridylmethyl 378 H 3-Pyridylmethyl 379 H Perfuryloxy 380 H Thienylmethoxy 381 H 3-hexazolylmethoxy 382 H 2-Oxazolylmethoxy 383 H 2-Pyridylmethoxy 384 H 2′-Furyl-2-ethenyl 385 H 2′-Thienyl-2-ethenyl 386 H 3′-Pyridyl-2-ethenyl 387 H Oxiramyl 388 H 1-Aziridinyl 389 H 1-Azazidinyl 390 H 1-Pyrrodidinyl 391 H 2-Tetrahydrofuryl 392 H 2-Tetrahydropyraryl 393 H 3-Tetrahydropyraryl 394 H 1-Piperidinyl 395 H 1-Morpholinyl 396 H 1-Piperazinyl 397 H 1,3-Dioxan-2-yl 398 H 3-Tetrahydrothiopyranyl 399 H 2-Dihydropyranyloxy 400 H 2-Tetrahydropyranyloxy 401 H CF₃ 402 H 2-Fluoroethyl 403 H 2,2,2-Trifluoroethyl 404 H Pentafluoroethyl 405 H Chloromethyl 406 H Dichloromethyl 407 H Trichloromethyl 408 H 2-Chloroethyl 409 H 2,2,2-Trichloroethyl 410 H Pentachloroethyl 411 H Cyclopropyl 412 H Cyclobutyl 413 H Cyclopentyl 414 H Cyclohexyl 415 H 1-Methylcyclopropyl 416 H 2,2-Dimethylcyclopropyl 417 H 1-Methylcyclohexyl 418 H 2,2-Difluorocyclopropyl 419 H 2,2-Dichlorocyclopropyl 420 H 2,2-Dibromocyclopropyl 421 H 2,2-Dichloro-3-methylcyclo- propyl 422 H 2,2,3,3-Tetrafluorocyclobutyl 423 H Ethenyl 424 H 1-Propenyl 425 H 2-Methyl-1-propenyl 426 H 4-Methylpent-3-en-1-yl 427 H 2-Propenyl 428 H 2-Butenyl 429 H 1-Methyl-2-propenyl 430 H 3-Methyl-2-butenyl 431 H 2,2-Difluoroethenyl 432 H 2,2-Dichloroethenyl 433 H 3,3,3-Trifluoropropenyl 434 H 3,3,3-Trichloropropenyl 435 H 3-Chloro-2-propenyl 436 H Cyclopent-1-enyl 437 H Cyclopentadienyl 438 H Cyclohex-1-enyl 439 H Pentafluorocyclopentadienyl 440 H Pentachlorocyclopentadienyl 441 H 4-Dimethylaminophenyl m.p.: 70-71° C. 442 H 4-Allyloxyphenyl m.p.: 81-83° C. 443 H Diphenylmethyl m.p.: 66-68° C. 444 H Dimethylbenzyl ¹H—NMR (CDCl₃): δ = 1.45s 3.78s, 4.03s, 5.00s, 7.17-7.41m

TABLE VII

No. R⁸ _(n) Data 1 H m.p. 156-158° C. 2 3-Fluoro 3 4-Fluoro 4 3-Chloro 5 4-Chloro 6 3-Bromo 7 4-Bromo 8 3-Iodo 9 4-Iodo 10 3,4-Dichloro 11 3,5-Dichloro 12 3,6-Dichloro 13 4,5-Dichloro 14 3,4,5-Trichloro 15 3,4,6-Trichloro 16 3,4,5,6-Tetrachloro 17 3,4,5,6-Tetrafluoro 18 3,4,5,6-Tetrabromo 19 3,5-Difluoro 20 3,5-Dibromo 21 3-Methyl 22 4-Methyl 23 3-Ethyl 24 4-Ethyl 25 3-iso-Propyl 26 4-iso-Propyl 27 3-tert.-Butyl 28 4-tert.-Butyl 29 3,4-Dimethyl 30 3,5-Dimethyl 31 3,6-Dimethyl 32 4,5-Dimethyl 33 3,4,5-Trimethyl 34 3,4,6-Trimethyl 35 3,4,5,6-Tetramethyl 36 3-Nitro 37 4-Nitro 38 3,5-Dinitro 39 3-Cyano 40 4-Cyano 41 3-Methoxy 42 4-Methoxy 43 3-tert.-Butoxy 44 4-tert.-Butoxy 45 3-Trifluoromethyl 46 4-Trifluoromethyl 47 3-Chloromethyl 48 4-Chloromethyl 49 3-Trifluoromethoxy 50 4-Trifluoromethoxy 51 3-Benzyloxy 52 4-Benzyloxy 53 4,5-Dibenzyloxy 54 3-Phenoxy 55 4-Phenoxy 56 3-Phenyl 57 4-Phenyl 58 3-Pyrid-2′-yl 59 4-Pyrid-2′-yl 60 3-Pyrid-2′-yloxy 61 4-Pyrid-2′-yloxy

TABLE VIII

No. R⁸ _(n) Data 1 H m.p. 152-155° C. 2 3-Fluoro 3 4-Fluoro 4 3-Chloro 5 4-Chloro 6 3-Bromo 7 4-Bromo 8 3-Iodo 9 4-Iodo 10 3,4-Dichloro 11 3,5-Dichloro 12 3,6-Dichloro 13 4,5-Dichloro 14 3,4,5-Trichloro 15 3,4,6-Trichloro 16 3,4,5,6-Tetrachloro 17 3,4,5,6-Tetrafluoro 18 3,4,5,6-Tetrabromo 19 3,5-Difluoro 20 3,5-Dibromo 21 3-Methyl 22 4-Methyl 23 3-Ethyl 24 4-Ethyl 25 3-iso-Propyl 26 4-iso-Propyl 27 3-tert-Butyl 28 4-tert-Butyl 29 3,4-Dimethyl 30 3,5-Dimethyl 31 3,6-Dimethyl 32 4,5-Dimethyl 33 3,4,5-Trimethyl 34 3,4,6-Trimethyl 35 3,4,5,6-Tetramethyl 36 3-Nitro 37 4-Nitro 38 3,5-Dinitro 39 3-Cyano 40 4-Cyano 41 3-Methoxy 42 4-Methoxy 43 3-tert.Butoxy 44 4-tert.Butoxy 45 3-Trifluoromethyl 46 4-Trifluoromethyl 47 3-Chloromethyl 48 4-Chloromethyl 49 3-Trifluoromethoxy 50 4-Trifluoromethoxy 51 3-Benzyloxy 52 4-Benzyloxy 53 4,5-Dibenzyloxy 54 3-Phenoxy 55 4-Phenoxy 56 3-Phenyl 57 4-Phenyl 58 3-Pyrid-2′-yl 59 4-Pyrid-2′-yl 60 3-Pyrid-2′-yloxy 61 4-Pyrid-2′-yloxy

TABLE IX

No. X Y R¹ R⁸ Data 1 CH—SCH₃ O CH₃ H 2 CH—SCH₃ NH CH₃ H 3 CH—SCH₃ S CH₃ H 4 CH₂ O CH₃ H 5 CH₂ NH CH₃ H 6 CH₂ S CH₃ H 7 CH—CH₃ O CH₃ H 8 CH—CH₃ NH CH₃ H 9 CH—CH₃ S CH₃ H 10 CH—CH₃ O CH₃ Perchloro 11 CH—CH₃ NH CH₃ Perchloro 12 CH—CH₃ S CH₃ Perchloro 13 CH—OCH₃ NH CH₃ H 14 CH—OCH₃ S CH₃ H 15 CH—OCH₃ NH CH₃ Perchloro 16 CH—OCH₃ S CH₃ Perchloro 17 N—OCH₃ NH CH₃ H 18 N—OCH₃ S CH₃ H 19 N—OCH₃ NH CH₃ Perchloro 20 N—OCH₃ S CH₃ Perchloro

In general terms, the novel compounds are extremely effective on a broad spectrum of phytopathogenic fungi, in particular those from the class consisting of the Ascomycetes and Basidiomycetes. Some of them have a systemic action and can be used as foliar and soil fungicides.

The fungicidal compounds are of particular interest for controlling a large number of fungi in various crops or their seeds, especially wheat. rye, barley, oats, rice, indian corn, lawns, cotton, soybeans, coffee, sugar cane, fruit and ornamentals in horticulture and viticulture, and in vegetables such as cucumbers, beans and cucurbits.

The novel compounds are particularly useful for controlling the following plant diseases:

Erysiphe graminis in cereals,

Erysiphe cichoracearum and Sphaerotheca fuliginea in curcurbits,

Podosphaera leucotricha in apples,

Uncinula necator in vines,

Puccinia species in cereals,

Rhizoctonia solani in cotton,

Ustilago species in cereals and sugar cane,

Venturia inaequalis scab in apples,

Helminthosporium species in cereals,

Septoria nodorum in wheat,

Botrytis cinerea gray mold in strawberries and grapes,

Cercospora arachidicola in groundnuts,

Pseudocercosporella herpotrichoides in wheat and barley,

Pyricularia oryzae in rice,

Phytophthora infestans in potatoes and tomatoes,

Fusarium and Verticillium species in various plants,

Plasmopara viticola in grapes,

Alternaria species in fruit and vegetables.

The compounds are applied by spraying or dusting the plants with the active ingredients, or treating the seeds of the plants with the active ingredients. They may be applied before or after infection of the plants or seeds by the fungi. Either the fungi themselves, or the plants seed or materials to be protected against fungus attack, or the soil are treated with a fungicidally effective amount of the active ingredient.

The novel substances can be converted into conventional formulations such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application forms depend entirely on the purposes for which they are intended they should at all events ensure a fine and uniform distribution of the active ingredient. The formulations are produced in known manner, for example by extending the active ingredient with solvents and/or carriers, with or without the use of emulsifiers and dispersants; if water is used as solvent, it is also possible to employ other organic solvents as auxiliary solvents. Suitable auxiliaries for this purpose are solvents such as aromatics (e.g., xylene), chlorinated aromatics (e.g., chlorobenzenes), paraffins (e.g., crude oil fractions), alcohols (e.g., methanol, butanol), ketones (e.g., cyclohexanone), amines (e.g., ethanolamine, dimethylformamide), and water; carriers such as ground natural minerals (e.g., kaolins, aluminas, talc and chalk) and ground synthetic minerals (e.g., highly disperse silica and silicates); emulsifiers such as nonionic and anonic emulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates); and dispersants such as ligninsulfite waste liquors and methylcellulose.

The fungicides generally contain from 0.1 to 95, and preferably from 0.5 to 90, wt % of active ingredient. The application rates are from 0.02 to 3 kg or more of active ingredient per hectare, depending on the type of effect desired. The novel compounds may also be used for protecting materials, e.g., on Paecilomyces variotii. When the active ingredients are used for treating seed, amounts of from 0.001 to 50, and preferably from 0.01 to 10, g per kg of seed are generally required.

The agents and the ready-to-use formulations prepared from them, such as solutions, emulsions, suspensions, powders, dusts, pastes and granules, are applied in conventional manner, for example by spraying, atomizing, dusting, scattering, dressing or watering.

Examples of formulations are given below.

I. A solution of 90 parts by weight of compound no. 429 (Table I) and 10 parts by weight of N-methyl-α-pyrrolidone, which is suitable for application in the form of very fine drops.

II. A mixture of 20 parts by weight of compound no. 14 (Table II), 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By finely dispersing the mixture in water, an aqueous dispersion is obtained.

III. An aqueous dispersion of 20 parts by weight of compound no. 49 (Table I), 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By finely dispersing the solution in water, an aqueous dispersion is obtained.

IV. An aqueous dispersion of 20 parts by weight of compound no. 56 (Table I), 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210° and 280° C., and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By finely distributing the solution in water, an aqueous dispersion is obtained.

V. A hammer-milled mixture of 80 parts by weight of compound no. 14 (Table I), 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 10 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and 7 parts by weight of powdered silica gel. By finely dispersing the mixture in water, a spray liquor is obtained.

VI. An intimate mixture of 3 parts by weight of compound no. 17 (Table II) and 97 parts by weight of particulate kaolin. The dust contains 3 wt % of the active ingredient.

VII. An intimate mixture of 30 parts by weight of compound no. 17 (Table I), 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil sprayed onto the surface of this silica gel. This formulation of the active ingredient exhibits good adherence.

VIII. A stable aqueous dispersion of 40 parts by weight of compound no. 571 (Table I), 10 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts by weight of water, which dispersion can be further diluted.

IX. A stable oily dispersion of 20 parts by weight of compound no. 616 (Table I), 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of a fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil.

In these application forms, the agents according to the invention may also be present together with other active ingredients, for example herbicides, insecticides, growth regulators, and fungicides, and may furthermore be mixed and applied together with fertilizers. Admixture with other fungicides frequently results in a greater fungicidal action spectrum.

USE EXAMPLES

The active ingredient used for comparison purposes was 2-(phenoxymethyl)-phenylglyoxylic acid-methyl ester-O-methyloxime (A) disclosed in EP 253,213.

USE EXAMPLE 1 Action on Wheat Brown Rust

Leaves of pot-grown wheat seedlings of the “Kanzler” variety were dusted with spores of brown rust (Puccinia recondita). The pots were then placed for 24 hours at 20° to 22° C. in a high-humidity (90-95%) chamber. During this period the spores germinated and the germ tubes penetrated the leaf tissue. The infected plants were then sprayed to runoff with aqueous liquors containing (dry basis) 80% of active ingredient and 20% of emulsifier. After the sprayed-on layer had dried, the plants were set up in the greenhouse at 20° to 22° C. and a relative humidity of 65 to 70%. The extent of rust fungus spread on the leaves was assessed after 8 days.

The results show that active ingredients nos. 49, 429, 56, 14, 15, 16, 17, 582, 578, 573, 592, 571, 704, 705 and 616 from Table I and nos. 17 and 644 from Table II, applied as 0.025 wt % spray liquors, have a better fungicidal action (95%) than prior art comparative compound A (50%).

USE EXAMPLE 2 Action on Pyricularia oryzae (Protective)

Leaves of pot-grown rice seedlings of the “Bahia” variety were sprayed to runoff with aqueous emulsions containing (dry basis) 80% of active ingredient and 20% of emulsifier, and inoculated 24 hours later with an aqueous spore suspension of Pyricularia oryzae. The plants were then set up in climatic cabinets at 22° to 24° C. and 95 to 99% relative humidity. The extent of fungus attack was assessed after 6 days.

The results show that active ingredients nos. 429, 583, 593, 592, 571, 706 and 616 from Table I and nos. 14, 15, 16, 17, 582, 592, 571, 769, 782, 672, 644 and 583 from Table II, applied as 0.05 wt % spray liquors, have a very good fungicidal action (100%).

The novel compounds are also suitable for effectively combating pests such as insects, arachnids and nematodes. They may be used as pesticides in crop protection and in the hygiene, stores protection and veterinary sector.

Examples of injurious insects belonging to the Lepidoptera order are Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Oendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholita funebrana, Grapholita molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keifferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flamea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scarbra, Plutella xylostella, rseudoplusia includens, Phyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerelella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis.

Examples from the Coleoptera order are Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Sruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Oiabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Onlema oryzae, Ortiorrhynchus sulcatus, Ortiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sltona lineatus and Sitophilus granaria.

Examples from the Diptera order are Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, oacus aleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossia morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea and Tipula paludosa.

Examples from the Thysanoptera order are Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci.

Examples from the Hymenoptera order are Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta.

Examples from the Heteroptera order are Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Oysdercus cingulatus, Oysdercus intermedius, Eurygaster integriceps, Euchistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis and Thyanta perditor.

Examples from the nematodes class are root-knot nematodes, e.g., Meloidogyne hapla, Meloidogyne incognita and Meloidogyne javanica, cyst-forming nematodes, e.g., Globodera rostochiensis, Heterodera avenae, Hetrodera glycinae, Heterodera schachtii and Heterodera trifolii, and stem and leaf eelworms, e.g., Belonolaimus longicaudatus, Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multicinctus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus and Pratylenchus goodeyi.

When the active ingredients are used for combating pests, the concentrations in the finished formulations may vary over a wide range. Generally, the concentration is from 0.0001 to 10, and preferably from 0.001 to 0.1%.

The active ingredients may also be successfully used in the ultra-low-volume method (ULV), where it is possible to apply formulations containing more than 95 wt % of active ingredient, or even the active ingredient without any additives.

When the active ingredients are used for combating pests in the open, the application rates are from 0.01 to 10, and preferably from 0.1 to 1.0, kg/ha.

USE EXAMPLE 3 Tetranychus telarius (Spider Mite); Contact Action—Spray Test

Potted bush beans which had developed the first pair of true leaves and were heavily infested with all stages of the spider mite Tetranychus telarius were sprayed to runoff in a spray cabinet with aqueous formulations of the active ingredients. The plants were placed on a rotating disc and sprayed from all sides with 50 ml of spray liquor. The plants were heavily infested with mites and numerous eggs had been laid on them. The action was assessed after 5 days by means of a binocular microscope. During this period, the plants were kept under normal greenhouse conditions.

Application rate Mortality Compound no. in ppm in % from Table I 49 100 80 36 100 80 43 1000 100 429 1000 100 38 40 100 39 100 100 45 1000 100 582 about 20 100 579 20 80 583 40 100 573 20 100 593 1000 80 592 40 100 704 about 20 100 705 40 100 from Table II 37 1000 100 39 1000 100 45 1000 100

USE EXAMPLE 4 Musca Domestica (Housefly); Continuous Contact Action

Both the tops and bottoms of Petri dishes 10 cm in diameter were lined with a total of 1 ml of acetonic solutions of the active ingredients. After the solvent had evaporated (about 30 mins.), 10 files and absorbent cotton steeped in water were introduced into each dish and the dishes closed. The flies in supine position were counted after 24 hours.

If a kill rate of 80 to 100% occurs at a concentration of 0.01 mg/dish, the test is continued with falling concentrations.

Compound no. Application rate Mortality from Table I in ppm in % 49 0.1 80 36 1.0 80 37 0.1 100 582 0.1 80 593 0.1 60 705 0.1 100 706 0.1 100

USE EXAMPLE 5 Plutella Maculipennis (Diamondback Moth); Ingestion-Inhibiting Action

Young kohlrabi leaves are dipped for 3 seconds into aqueous solutions of the candidate compounds, and then placed on a round filter paper 9 cm in diameter which has been moistened with 0.5 ml of water. The filter paper is then placed in a Petri dish 10 cm in diameter. 10 caterpillars in the 4th larval stage are then placed on each leaf and the Petri dish is closed. Ingestion inhibition is determined in % after 48 hours.

Compound no. Application rate Mortality from Table I in ppm in % 49 200 80 36 200 80 429 1000 80 16 400 80 582 400 100 593 1000 80 592 400 80 705 400 80 706 400 80

USE EXAMPLE 6 Action on Peronospora in Grapes

Leaves of potted vines of the “Müller Thurgau” variety were sprayed with aqueous liquors containing (dry basis) 80% of active ingredient and 20% of emulsifier. To assess the duration of action of the active ingredients, the plants were, after the sprayed-on layer had dried, set up in the greenhouse for 8 days. Only then were the leaves infected with a zoospore suspension of Plasmopara viticola. The vines were then placed for 48 hours in a water-vapor-saturated chamber at 24° C. and then for 5 days in a greenhouse at from 20° to 30° C. To accelerate the sporangiophore discharge, the plants were then again set up in the moist chamber for 16 hours. The extent to which the leaves had been attacked was then assessed.

The results show that active ingredients nos. 49, 429, 56, 14, 15, 16, 17, 582, 578, 573, 592, 571, 704, 705, 616, 117, 156, 579, 583, 593 and 706 from Table I, nos. 17, 644, 117, 429, 56, 43, 36, 49, 14, 15, 16, 582, 614 and 672 from Table II, and compound no. 1 from Table VII have, when applied as 0.025 wt % spray liquors a better fungicidal action (95%) than the prior art comparative agent A (50%). 

We claim:
 1. O-benzyloxime ether of the formula I

where X is N—C₁-C₄alkoxy, Y is O or NR⁵, R¹, R² and R⁵ are H or C₁-C₄-alkyl, Z¹ and Z² are identical or different and each is H, halogen, methyl, methoxy or cyano, R³ and R⁴ are identical or different and each is hydrogen, cyano, straight-chain or branched C₁-C₁₀-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl, arylthio-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₅-haloalkenyl, C₃-C₆-cycloalkenyl, C₃-C₆-halocycloalkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₄-alkylthio, benzylthio, C₁-C₄-alkylcarbonyl, substituted or unsubstituted phenylcarbonyl, substituted or unsubstituted benzylcarbonyl, C₁-C₄-alkoxycarbonyl, substituted or unsubstituted phenoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted aryl-C₁-C₄-alkyl, substituted or unsubstituted aryl-C₂-C₄-alkenyl, substituted or unsubstituted aryloxy-C₁-C₄-alkyl, or substituted or unsubstituted arylthio-C₁-C₄-alkyl, N(R⁶)₂, where the radicals R⁶ are identical or different and each is H, C₁-C₆-alkyl or substituted or unsubstituted phenyl, —CO—N(R⁷)₂, where the radicals R⁷ are identical or different and each is H or C₁-C₄-alkyl, substituted or unsubstituted meaning, in addition to hydrogen, the radicals halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, C₁-C₁₀-alkoximino-C₁-C₂-alkyl, aryl, aryloxy, benzyloxy, or C₃-C₆-cycloalkyl, or R³ and R⁴ together with the carbon atom to which they are attached form cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, camphenyl, tetralyl, idanyl or fluorenyl, each of which may be substituted by the radicals stated above under substituted or unsubstituted, or R³ and R⁴ may be halogen; and “aryl”, alone or as part of another radical, is phenyl, naphthyl, or anthryl.
 2. O-Benzyloxime ethers of the formula III

where the radicals R³ and R⁴ have the meanings given in claim
 1. 3. A compound of the formula I as set forth in claim 1, wherein X is NOCH₃ or NOC₂H₅, Y is 0, R¹ is C₁-C₄-alkyl, R₂ is H or C₁-C₂-alkyl, R₃ and R₄ are identical or different and each is hydrogen, cyano, straight-chain or branched C₁-C₁₀-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkylthio-C₁-C₄-alkyl, arylthio-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₂-C₄-haloalkenyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted aryl-C₁-C₄-alkyl, or substituted or unsubstituted aryl-C₂-C₄-alkenyl, N(R⁶)₂, where R⁶ is identical or different and each is H, C₁-C₆-alkyl, C₃-C₆-cycloalkyl or substituted or unsubstituted phenyl, CO—N(R⁷)₂, where R⁷ is identical or different and each is H or C₁-C₄-alkyl; or R³ and R⁴ together with the carbon atom to which they are attached form cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, camphenyl, tetralyl, indanyl, or fluorenyl, each of which may be substituted by the radicals given under substituted or unsubstituted, or R³ or R⁴ may be halogen; Z¹ and Z² are each hydrogen; and substituted or unsubstituted and aryl have the meanings given in claim
 1. 4. A fungicidal composition comprising in inert carrier and a fungicidally effective amount of an O-benzyloxime ether of the formula I

according to claim
 1. 5. A process for combating fungi, wherein the fungi, or the materials, plants or seed threatened by fungus attack, or the soil, are treated with a fungicidally effective amount of a compound of the formula I

according to claim
 1. 6. A compound of the formula I as set forth in claim 1, wherein R¹ is methyl, R² is H, R³ is CN, R⁴ is cyclopropyl, X is N—OCH₃, Y is O, and Z¹ and Z² are hydrogen.
 7. A compound according to claim 1, wherein Y is NR⁵.
 8. A compound according to claim 7 10, wherein R¹ is methyl, Z¹, Z², R² and R⁵ are hydrogen, X is NOCH₃, R³ is methyl, and R⁴ is 3,5-dichlorophenyl.
 9. O-benzyloxime ether of the formula I

where X is N—C₁-C₄-alkoxy, Y is O, R¹ is C₁-C₄-alkyl, R², Z¹ and Z² are H, R³ is hydrogen, methyl, ethyl, propyl or cyano, R⁴ is hydrogen, cyano, straight-chain or branched C₁-C₁₀-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl, arylthio-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₅-haloalkenyl, C₃-C₆-cycloalkenyl, C₃-C₆-halocycloalkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₄-alkylthio, benzylthio, C₁-C₄-alkylcarbonyl, substituted or unsubstituted phenylcarbonyl, substituted or unsubstituted benzylcarbonyl, C₁-C₄-alkoxycarbonyl, substituted or unsubstituted phenoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl, aryl substituted by C₁-C₁₀-alkoximino-C₁-C₂-alkyl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted aryl-C₁-C₄-alkyl, substituted or unsubstituted aryl-C₂-C₄-alkenyl, substituted or unsubstituted aryloxy-C₁-C₄-alkyl, or substituted or unsubstituted arylthio-C₁-C₄-alkyl, N(R⁶)₂, where the radicals R⁶ are identical or different and each is H, C₁-C₆-alkyl or substituted or unsubstituted phenyl, —CO—N(R⁷)₂, where the radicals R⁷ are identical or different and each is H or C₁-C₄-alkyl, substituted or unsubstituted meaning, in addition to hydrogen, the radicals halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, C₁-C₁₀-alkoximino-C₁-C₂-alkyl, aryl, aryloxy, benzyloxy, or C₃-C₆-cycloalkyl, or R³ and R⁴ together with the carbon atom to which they are attached form cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, camphenyl, tetralyl, indanyl or fluorenyl, each of which may be substituted by the radicals stated above under substituted or unsubstituted, or R³ or R⁴ may be halogen, and “aryl”, alone or as part of another radical, is phenyl, naphthyl, or anthryl.
 10. O-benzyloxime ether of the formula I

where X is N—C ₁ -C ₄-alkoxy Y is NR ⁵, R ¹ , R ² and R ⁵ are H or C ₁ -C ₄-alkyl, Z ¹ and Z ² are identical or different and each is H, halogen, methyl, methoxy or cyano, R ³ and R ⁴ are identical or different and each is hydrogen, cyano, straight-chain or branched C ₁ -C ₁₀-alkyl, C ₁ -C ₄-haloalkyl, C ₃ -C ₆-cycloalkyl, C ₃ -C ₆-halocycloalkyl, C ₃ -C ₆-cycloalkyl-C ₁ -C ₄-alkyl, C ₁ -C ₄-alkoxy-C ₁ -C ₄-alkyl, C ₁ -C ₄-alkylthio-C ₁ -C ₄-alkyl, arylthio-C ₁ -C ₄-alkyl, C ₂ -C ₆-alkenyl, C ₂ -C ₅-haloalkenyl, C ₃ -C ₆-cycloalkenyl, C ₃ -C ₆-halocycloalkenyl, C ₂ -C ₆-alkynyl, C ₁ -C ₆-alkoxy, C ₁ -C ₆-haloalkoxy, C ₁ -C ₄-alkylthio, benzylthio, C ₁ -C ₄-alkylcarbonyl substituted or unsubstituted phenylcarbonyl, substituted or unsubstituted benzylcarbonyl, C ₁ -C ₄-alkoxycarbonyl, substituted or unsubstituted phenoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted aryl-C ₁ -C ₄-alkyl, substituted or unsubstituted aryl-C ₂ -C ₄-alkenyl, substituted or unsubstituted aryloxy-C ₁ -C ₄-alkyl, or substituted or unsubstituted arylthio-C ₁ -C ₄-alkyl, N(R ⁶)₂ , where the radicals R ⁶ are identical or different and each is H, C ₁ -C ₆-alkyl or substituted or unsubstituted phenyl, —CO—N(R ⁷)₂ , where the radicals R ⁷ are identical or different and each is H or C ₁ -C ₄-alkyl, substituted or unsubstituted meaning, in addition to hydrogen, the radicals halogen, cyano, nitro, C ₁ -C ₄-alkyl, C ₁ -C ₄-alkoxy, C ₁ -C ₄-haloalkyl, C ₁ -C ₄-haloalkoxy, C ₁ -C ₁₀-alkoximino-C ₁ -C ₂-alkyl, aryl, aryloxy, benzyloxy, or C ₃ -C ₆-cycloalkyl, or R ³ and R ⁴ together with the carbon atom to which they are attached form cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, camphenyl, tetralyl, indanyl or fluorenyl, each of which may be substituted by the radicals stated above under substituted or unsubstituted or R ³ or R ⁴ may be halogen; and “aryl”, alone or as part of another radical, is phenyl, naphthyl, or anthryl.
 11. The O-benzyloxime ether of claim 10 , wherein R ² is hydrogen.
 12. O-Benzyloxime ethers of the formula II

where X is N—C ₁ -C ₄ alkoxy, R ¹ and R ⁵ are H or C ₁ -C ₄-alkyl, Z ¹ and Z ² are identical or different and each is H, halogen, methyl, methoxy or cyano, R ³ is cyano, and R ⁴ is substituted or unsubstituted phenyl or naphthyl, and the substituents on the phenyl or naphthyl are halogen, cyano, nitro, C ₁ -C ₄-alkyl, C ₁ -C ₄-alkoxy, C ₁ -C ₄-haloalkyl, C ₁ -C ₄-haloalkoxy, C ₁ -C ₁₀-alkoximino-C ₁ -C ₂-alkyl, aryl, aryloxy, benzyloxy, or C ₃ -C ₆-cycloalkyl.
 13. A fungicidal composition comprising an inert carrier and a fungicidally effective amount of an O-benzyloxime ether of the formula I

according to claim 10 .
 14. A process for combating fungi, wherein the fungi, or the materials, plants, or seed threatened by fungus attack or the soil, are treated with a fungicidally effective amount of a compound of the formula I

according to claim 10 . 